@article{HermannsSchmidt2017,
  author    = {Hermanns, Jolanda and Schmidt, Bernd},
  title     = {Zur Verwendung von QR-Codes in Uni-Seminaren - ein Baustein in den neu konzipierten {\"U}bungen zur Vorlesung „Organische Chemie f{\"u}r Studierende im Nebenfach"},
  series = {Chemkon},
  volume    = {24},
  journal   = {Chemkon},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {0944-5846},
  doi       = {10.1002/ckon.201710300},
  pages     = {139 -- 141},
  year      = {2017},
  abstract  = {Die Verwendung von QR-Codes in Begleitseminaren zur Vorlesung „Organische Chemie" f{\"u}r Studierende mit Chemie im Nebenfach wird vorgestellt. Die Hausaufgaben zu den Seminaren wurden mit einem QR-Code versehen. Dieser f{\"u}hrt zu weiterf{\"u}hrenden Hilfen. Der Einsatz der QR-Codes sowie die Neukonzeption der Seminare wurden evaluiert.},
  language  = {de}
}
@article{SchmidtStaude2006,
  author    = {Schmidt, Bernd and Staude, Lucia},
  title     = {Unexpected transfer hydrogenation of C-C-double bonds during Tandem-RCM-isomerization reactions},
  series = {Journal of organometallic chemistry},
  volume    = {691},
  journal   = {Journal of organometallic chemistry},
  number    = {24-25},
  publisher = {Elsevier},
  address   = {Lausanne},
  issn      = {0022-328X},
  doi       = {10.1016/j.jorganchem.2006.07.011},
  pages     = {5218 -- 5221},
  year      = {2006},
  abstract  = {Unexpected hydrogen transfer from 2-propanol to C-C-double bonds has been observed in the course of a Tandem RCM-isomerization reaction leading to sterically congested spirocycles.},
  language  = {en}
}
@article{KwesigaKellingKerstingetal.2020,
  author    = {Kwesiga, George and Kelling, Alexandra and Kersting, Sebastian and Sperlich, Eric and von Nickisch-Rosenegk, Markus and Schmidt, Bernd},
  title     = {Total syntheses of prenylated isoflavones from Erythrina sacleuxii and their antibacterial activity},
  series = {Journal of natural products},
  volume    = {83},
  journal   = {Journal of natural products},
  number    = {11},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0163-3864},
  doi       = {10.1021/acs.jnatprod.0c00932},
  pages     = {3445 -- 3453},
  year      = {2020},
  abstract  = {The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4'-methoxy-3'-prenylisoflavone) and erysubin F (7,4'-dihydroxy-8,3'-diprenylisoflavone) were synthesized for the first time, starting from mono-or di-O-allylated chalcones, and the structure of 5-deoxy-3'-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4'-dihydroxy-8,3'-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4'-dihydroxy-8,3'-diprenylflavone (27), and 5-deoxy-3'prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 mu M. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4'-dihydroxy-8,3'diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 mu M, respectively. In contrast, the monoprenylated 5-deoxy-3'-prenylbiochanin A (7) is inactive against this MRSA strain.},
  language  = {en}
}
@article{PazHeydenreichSchmidtetal.2018,
  author    = {Paz, Cristian and Heydenreich, Matthias and Schmidt, Bernd and Vadra, Nahir and Baggio, Ricardo},
  title     = {Three new dihydro-beta-agarofuran sesquiterpenes from the seeds of Maytenus boaria},
  series = {Acta Crystallographica Section C},
  volume    = {74},
  journal   = {Acta Crystallographica Section C},
  publisher = {International Union of Crystallography},
  address   = {Chester},
  issn      = {2053-2296},
  doi       = {10.1107/S2053229618005429},
  pages     = {564 -- 570},
  year      = {2018},
  abstract  = {As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new beta-agarofuran sesquiterpenes, namely (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9-dihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b] oxepine-5,10-diylbis(furan-3-carboxylate), C27H32O11, (II), (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-9-hydroxy-2,2,5a, 9-tetramethyloctahydro-2H-3,9a-methanobenzo[ b] oxepine-5,10-diyl bis(furan-3-carboxylate), C27H32O10, (III), and (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-10-(benzoyloxy)-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, C29H34O9, (IV), obtained from the seeds of Maytenus boaria and closely associated with a recently published relative [Paz et al. (2017). Acta Cryst. C73, 451-457]. In the (isomorphic) structures of (II) and (III), the central decalin system is esterified with an acetate group at site 1 and furoate groups at sites 6 and 9, and differ at site 8, with an OH group in (II) and no substituent in (III). This position is also unsubstituted in (IV), with site 6 being occupied by a benzoate group. The chirality of the skeletons is described as 1S, 4S, 5S, 6R, 7R, 8R, 9R, 10S in (II) and 1S, 4S, 5S, 6R, 7R, 9S, 10S in (III) and (IV), matching the chirality suggested by NMR studies. This difference in the chirality sequence among the title structures (in spite of the fact that the three skeletons are absolutely isostructural) is due to the differences in the environment of site 8, i.e. OH in (II) and H in (III) and (IV). This diversity in substitution, in turn, is responsible for the differences in the hydrogen-bonding schemes, which is discussed.},
  language  = {en}
}
@article{RiemerRiemerKruegeretal.2021,
  author    = {Riemer, Nastja and Riemer, Martin and Kr{\"u}ger, Mandy and Clarkson, Guy J. and Shipman, Michael and Schmidt, Bernd},
  title     = {Synthesis of arylidene-beta-lactams via exo-selective Matsuda-Heck arylation of methylene-beta-lactams},
  series = {The journal of organic chemistry : JOC},
  volume    = {86},
  journal   = {The journal of organic chemistry : JOC},
  number    = {13},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.1c00638},
  pages     = {8786 -- 8796},
  year      = {2021},
  abstract  = {exo-Methylene-beta-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)-propionic acid and reacted with arene diazonium salts in a Heck-type arylation in the presence of catalytic amounts of Pd(OAc)(2) under ligand-free conditions. The products, arylidene-beta-lactams, were obtained in high yields as single isomers. The beta-hydride elimination step of the Pd-catalyzed coupling reaction proceeds with high exo-regioselectivity and E-stereoselectivity. With aryl iodides, triflates, or bromides, the coupling products were isolated only in low yields, due to extensive decomposition of the starting material at elevated temperatures. This underlines that arene diazonium salts can be superior arylating reagents in Heck-type reactions and yield coupling products in synthetically useful yields and selectivities when conventional conditions fail.},
  language  = {en}
}
@article{NchiozemNgnitedemSperlichMatietaetal.2023,
  author    = {Nchiozem-Ngnitedem, Vaderament-Alexe and Sperlich, Eric and Matieta, Valaire Yemene and Kuete, Jenifer Reine Ngnouzouba and Kuete, Victor and Omer, Ejlal A. A. and Efferth, Thomas and Schmidt, Bernd},
  title     = {Synthesis and bioactivity of isoflavones from ficus carica and some non-natural analogues},
  series = {Journal of natural products : Lloydia},
  volume    = {86},
  journal   = {Journal of natural products : Lloydia},
  number    = {6},
  publisher = {American Chemical Society},
  address   = {Washington, DC},
  issn      = {0163-3864},
  doi       = {10.1021/acs.jnatprod.3c00219},
  pages     = {1520 -- 1528},
  year      = {2023},
  abstract  = {FicucariconeD (1) and its 4 '-demethyl congener 2 are isoflavones isolated from fruits of Ficus carica that share a 5,7-dimethoxy-6-prenyl-substituted A-ring. Both naturalproducts were, for the first time, obtained by chemical synthesisin six steps, starting from 2,4,6-trihydroxyacetophenone. Key stepsare a microwave-promoted tandem sequence of Claisen- and Cope-rearrangementsto install the 6-prenyl substituent and a Suzuki-Miyaura crosscoupling for installing the B-ring. By using various boronic acids,non-natural analogues become conveniently available. All compoundswere tested for cytotoxicity against drug-sensitive and drug-resistanthuman leukemia cell lines, but were found to be inactive. The compoundswere also tested for antimicrobial activities against a panel of eightGram-negative and two Gram-positive bacterial strains. Addition ofthe efflux pump inhibitor phenylalanine-arginine-beta-naphthylamide(PA beta N) significantly improved the antibiotic activity in mostcases, with MIC values as low as 2.5 mu M and activity improvementfactors as high as 128-fold.},
  language  = {en}
}
@article{ZhaoSarhanEljarratetal.2022,
  author    = {Zhao, Yuhang and Sarhan, Radwan Mohamed and Eljarrat, Alberto and Kochovski, Zdravko and Koch, Christoph and Schmidt, Bernd and Koopman, Wouter-Willem Adriaan and Lu, Yan},
  title     = {Surface-functionalized Au-Pd nanorods with enhanced photothermal conversion and catalytic performance},
  series = {ACS applied materials \& interfaces},
  volume    = {14},
  journal   = {ACS applied materials \& interfaces},
  number    = {15},
  publisher = {American Chemical Society},
  address   = {Washington, DC},
  issn      = {1944-8244},
  doi       = {10.1021/acsami.2c00221},
  pages     = {17259 -- 17272},
  year      = {2022},
  abstract  = {Bimetallic nanostructures comprising plasmonic and catalytic components have recently emerged as a promising approach to generate a new type of photo-enhanced nanoreactors. Most designs however concentrate on plasmon-induced charge separation, leaving photo-generated heat as a side product. This work presents a photoreactor based on Au-Pd nanorods with an optimized photothermal conversion, which aims to effectively utilize the photo-generated heat to increase the rate of Pd-catalyzed reactions. Dumbbell-shaped Au nanorods were fabricated via a seed-mediated growth method using binary surfactants. Pd clusters were selectively grown at the tips of the Au nanorods, using the zeta potential as a new synthetic parameter to indicate the surfactant remaining on the nanorod surface. The photothermal conversion of the Au-Pd nanorods was improved with a thin layer of polydopamine (PDA) or TiO2. As a result, a 60\% higher temperature increment of the dispersion compared to that for bare Au rods at the same light intensity and particle density could be achieved. The catalytic performance of the coated particles was then tested using the reduction of 4-nitrophenol as the model reaction. Under light, the PDA-coated Au-Pd nanorods exhibited an improved catalytic activity, increasing the reaction rate by a factor 3. An analysis of the activation energy confirmed the photoheating effect to be the dominant mechanism accelerating the reaction. Thus, the increased photothermal heating is responsible for the reaction acceleration. Interestingly, the same analysis shows a roughly 10\% higher reaction rate for particles under illumination compared to under dark heating, possibly implying a crucial role of localized heat gradients at the particle surface. Finally, the coating thickness was identified as an essential parameter determining the photothermal conversion efficiency and the reaction acceleration.},
  language  = {en}
}
@article{SchmidtAudoersch2017,
  author    = {Schmidt, Bernd and Aud{\"o}rsch, Stephan},
  title     = {Stereoselective Total Syntheses of Polyacetylene Plant Metabolites via Ester-Tethered Ring Closing Metathesis},
  series = {The journal of organic chemistry},
  volume    = {82},
  journal   = {The journal of organic chemistry},
  number    = {3},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.6b02987},
  pages     = {1743 -- 1760},
  year      = {2017},
  abstract  = {Total syntheses of five naturally occurring polyacetylenes from three different plants are described. These natural products have in common an E,Z-configured conjugated diene linked to a di-or triyne chain. As the key method to stereoselectively establish the E,Z-diene part, an ester-tethered ring-closing metathesis/base-induced eliminative ring opening sequence was used. The results presented herein do not only showcase the utility of this tethered RCM variant but have also prompted us to suggest that the originally assigned absolute configurations of chiral polyacetylenes from Atractylodes macrocephala should be revised or at least reconsidered.},
  language  = {en}
}
@article{LoodSchmidt2020,
  author    = {Lood, Kajsa and Schmidt, Bernd},
  title     = {Stereoselective synthesis of conjugated polyenes based on tethered olefin metathesis and carbonyl olefination},
  series = {The journal of organic chemistry},
  volume    = {85},
  journal   = {The journal of organic chemistry},
  number    = {7},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.0c00446},
  pages     = {5122 -- 5130},
  year      = {2020},
  abstract  = {The combination of a highly stereoselective tethered olefin metathesis reaction and a Julia-Kocienski olefination is presented as a strategy for the synthesis of conjugated polyenes with at least one Z-configured C=C bond. The strategy is exemplified by the synthesis of the marine natural product (+)-bretonin B.},
  language  = {en}
}
@article{SchmidtNave2006,
  author    = {Schmidt, Bernd and Nave, Stefan},
  title     = {Stereoselective syntheses of enantiomerically pure 2,5-disubstituted dihydropyrans based on olefin metathesis},
  series = {The journal of organic chemistry},
  volume    = {71},
  journal   = {The journal of organic chemistry},
  number    = {19},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/jo061190k},
  pages     = {7364 -- 7369},
  year      = {2006},
  abstract  = {A short synthesis of 2,5-disubstituted dihydropyrans starting from D-mannitol as a chiral building block is described. Our synthetic approach combines ruthenium-catalyzed ring closing olefin metathesis and palladium-catalyzed nucleophilic substitution.},
  language  = {en}
}
@article{KwesigaSperlichSchmidt2021,
  author    = {Kwesiga, George and Sperlich, Eric and Schmidt, Bernd},
  title     = {Scope and applications of 2,3-oxidative aryl rearrangements for the synthesis of isoflavone natural products},
  series = {The journal of organic chemistry},
  volume    = {86},
  journal   = {The journal of organic chemistry},
  number    = {15},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.1c01375},
  pages     = {10699 -- 10712},
  year      = {2021},
  abstract  = {The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.},
  language  = {en}
}
@article{SandSchmidt2021,
  author    = {Sand, Patrick and Schmidt, Bernd},
  title     = {Ruthenium-catalyzed sulfoalkenylation of acetanilides and dual-use of the catalyst directing group},
  series = {European journal of organic chemistry},
  volume    = {2021},
  journal   = {European journal of organic chemistry},
  number    = {40},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.202101216},
  pages     = {5497 -- 5506},
  year      = {2021},
  abstract  = {In contrast to vinylsulfonates and vinylsulfones, vinylsulfonamides are unreactive in Pd-catalyzed oxidative Heck-coupling reactions with acetanilides. This limitation has been resolved by using a C-H-activation protocol based on Ru-Cu-Ag-catalysis. Overall, the Ru-Cu-Ag-catalyzed conditions turned out to be more reliable and showed better reproducibility than the Pd-catalyzed C-H-activation. The coupling products thus obtained are functionalized styrenyl sulfones and -sulfonamides which can be used as starting materials for the synthesis of sulfonyl pyrroles and sulfonyl pyrrolo[2,3-c]quinolines.},
  language  = {en}
}
@article{DebsharmaSchmidtLaschewskyetal.2021,
  author    = {Debsharma, Tapas and Schmidt, Bernd and Laschewsky, Andre and Schlaad, Helmut},
  title     = {Ring-opening metathesis polymerization of unsaturated carbohydrate derivatives},
  series = {Macromolecules : a publication of the American Chemical Society},
  volume    = {54},
  journal   = {Macromolecules : a publication of the American Chemical Society},
  number    = {6},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0024-9297},
  doi       = {10.1021/acs.macromol.0c02821},
  pages     = {2720 -- 2728},
  year      = {2021},
  abstract  = {A series of biomass-derived levoglucosenyl alkyl ethers (alkyl = methyl, ethyl, n-propyl, isopropyl, and n-butyl) were synthesized and polymerized by ring-opening olefin metathesis polymerization using the Grubbs catalyst C793 at room temperature. Polymerizations were successfully performed in conventional solvents such as 1,4-dioxane and dichloromethane as well as in polar aprotic "green" solvents such as 2-methyltetrahydrofuran, dihydrolevoglucosenone (Cyrene), and ethyl acetate. The prepared polyacetals with degrees of polymerization of similar to 100 exhibit Schulz-Flory-type molar mass distributions and are thermoplastic materials with rather low glass transition temperatures in the range of 43-0 degrees C depending on the length of the alkyl substituent. Kinetic studies revealed that the polymerization proceeded rapidly to a steady state with a certain minimum monomer concentration threshold. When the steady state was reached, just about half of the [Ru] catalyst had been effective to initiate the polymerization, indicating that the initiation step was a slow process. The remaining catalyst was still active and did no longer react with monomers but with in-chain double bonds, cutting the formed polymer chains into shorter fragments. In the long term, all catalyst was consumed and propagating [Ru] chain ends were deactivated by the elimination of [Ru] from the chain ends to form inactive chains with terminal aldehyde groups.},
  language  = {en}
}
@article{SchultzeSchmidt2018,
  author    = {Schultze, Christiane and Schmidt, Bernd},
  title     = {Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins},
  series = {Beilstein journal of organic chemistry},
  volume    = {14},
  journal   = {Beilstein journal of organic chemistry},
  publisher = {Beilstein-Institut zur F{\"o}rderung der Chemischen Wissenschaften},
  address   = {Frankfurt, Main},
  issn      = {1860-5397},
  doi       = {10.3762/bjoc.14.278},
  pages     = {2991 -- 2998},
  year      = {2018},
  abstract  = {8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.},
  language  = {en}
}
@article{SchultzeSchmidt2018,
  author    = {Schultze, Christiane and Schmidt, Bernd},
  title     = {Prenylcoumarins in One or Two Steps by a Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination/Cyclization Sequence},
  series = {The journal of organic chemistry},
  volume    = {83},
  journal   = {The journal of organic chemistry},
  number    = {9},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.8b00667},
  pages     = {5210 -- 5224},
  year      = {2018},
  abstract  = {The one-pot synthesis of 8-prenylcoumarins from 1,1-dimethylallylated salicylaldehydes and the stabilized ylide [(ethoxycarbonyl)methylene]triphenylphosphorane under microwave conditions was found to have a limited scope. The sequence suffers from a difficult and sometimes low-yielding synthesis of the precursors and from a competing deprenylation upon microwave irradiation. This side reaction occurs in particular with electron rich arenes with two or more alkoxy groups at adjacent positions, a prominent substitution pattern in naturally occurring 8-prenylcoumarins. Both limitations of this one-step sequence were overcome by a two-step synthesis consisting of a microwave-promoted tandem allyl ether Claisen rearrangement/Wittig olefination and a subsequent olefin cross metathesis with 2-methyl-2-butene. The cross metathesis step proceeds with a high selectivity and yields exclusively the desired prenyl, rather than the alternative crotyl substituent. Several naturally occurring 8-prenylcoumarins that were previously inaccessible have been synthesized in good overall yields along this route.},
  language  = {en}
}
@article{BehrendtHessLehmannetal.2019,
  author    = {Behrendt, Felix Nicolas and Hess, Andreas and Lehmann, Max and Schmidt, Bernd and Schlaad, Helmut},
  title     = {Polymerization of cystine-derived monomers},
  series = {Polymer Chemistry},
  volume    = {10},
  journal   = {Polymer Chemistry},
  number    = {13},
  publisher = {Royal Society of Chemistry},
  address   = {Cambridge},
  issn      = {1759-9954},
  doi       = {10.1039/c9py00118b},
  pages     = {1636 -- 1641},
  year      = {2019},
  abstract  = {Cystine was used as a platform chemical to prepare cyclic and acyclic monomers for entropy-driven ringopening polymerization (ED-ROMP) via olefin or disulfide metathesis and for step-growth polymerization. The olefin ED-ROMP of an olefin/disulfide containing 16-atom macrocycle using the 3rd generation Grubbs catalyst was examined in greater detail. Kinetic studies revealed that the catalyst turned inactive during the polymerization, which limited the achievable (apparent) polymer molar mass to similar to 70 kg mol(-1). Such limitation could be overcome with the disulfide ED-ROMP of the same macrocycle to yield polymers with molar masses of up to 180 kg mol(-1). The step-growth polymerizations of acyclic diene and dithiol monomers via olefin metathesis or oxidation were far less effective and yielded just low molar mass polymers or oligomers; photopolymerization of a thiol-ene monomer produced a polyester with a molar mass of 35 kg mol(-1).},
  language  = {en}
}
@article{SandSchmidt2021,
  author    = {Sand, Patrick and Schmidt, Bernd},
  title     = {Pd-catalyzed oxidative sulfoalkenylation of acetanilides and traceless removal of the catalyst directing group},
  series = {ChemistrySelect},
  volume    = {6},
  journal   = {ChemistrySelect},
  number    = {14},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {2365-6549},
  doi       = {10.1002/slct.202101009},
  pages     = {3563 -- 3567},
  year      = {2021},
  abstract  = {The palladium-catalyzed oxidative Heck-reaction, also referred to as Fujiwara-Moritani-reaction, has been investigated for the synthesis of styrenylsulfonyl compounds. Acetanilides and vinylsulfonyl compounds undergo dehydrogenative coupling reactions in moderate to quantitative yields, using benzoquinone as the oxidant of choice. Potassium peroxodisulfate, which had previously been identified as a superior oxidant for the coupling with acrylates, did not provide any coupling products with these olefins. Traceless removal of the catalyst directing group through a deacetylation-diazotation-coupling (DDC) sequence was demonstrated for 2-arylethene sulfones.},
  language  = {en}
}
@article{RiemerCoswigShipmanetal.2018,
  author    = {Riemer, Nastja and Coswig, Christin and Shipman, Michael and Schmidt, Bernd},
  title     = {Palladium-catalyzed cross-coupling of arenediazonium salts with organoindium or organobismuth reagents},
  series = {Synlett : accounts and rapid communications in synthetic organic chemistry},
  volume    = {29},
  journal   = {Synlett : accounts and rapid communications in synthetic organic chemistry},
  number    = {18},
  publisher = {Georg Thieme Verlag KG},
  address   = {Stuttgart},
  issn      = {0936-5214},
  doi       = {10.1055/s-0037-1611001},
  pages     = {2427 -- 2431},
  year      = {2018},
  abstract  = {Arylindium and isolated triarylbismuth compounds generated in situ react as nucleophiles with arenediazonium salts in palladium-catalyzed cross-coupling reactions to give substituted biphenyls.},
  language  = {en}
}
@article{HermannsSchmidtGlowinskietal.2020,
  author    = {Hermanns, Jolanda and Schmidt, Bernd and Glowinski, Ingrid and Keller, David},
  title     = {Online teaching in the course "organic chemistry" for nonmajor chemistry students},
  series = {Journal of chemical education},
  volume    = {97},
  journal   = {Journal of chemical education},
  number    = {9},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0021-9584},
  doi       = {10.1021/acs.jchemed.0c00658},
  pages     = {3140 -- 3146},
  year      = {2020},
  abstract  = {In this communication the development of an online course on the topic organic chemistry for nonmajor chemistry students is described and discussed. For this online course, the existing classroom course was further developed. New elements such as podcasts, task navigators, and a forum for discussing the solving of tasks or problems with the content were added. This new online course was evaluated. Therefore, a questionnaire was developed. This consists of questions with regard to the longtime learning behavior of the students and to the online learning. The results of this evaluation show that a preference for online learning and a preference for classroom teaching can be measured separately in two scales. Students values on the scale representing a preference for online learning correlate positively and significantly with confidence in the choice of the study subject, enthusiasm about the subject, and the ability to organize their learning, learning environment, and time management. They correlate also with the satisfaction concerning the materials provided. Students values for one of those teaching methods also correlate with their rating with regard to their exam preparation. Values representing a preference for online teaching correlate positively with students better feeling of exam preparation. Values representing a preference for classroom teaching show negative correlations with the values representing students similar or even better preparation for the exams as a result of online teaching. It is therefore not surprising that the ratings for the two scales correlate with the wish for a combination of online teaching and classroom teaching in the future. As a solution, a new course concept for the time after the corona virus crisis that suits all students is outlined in the outlook.},
  language  = {en}
}
@article{SchmidtRiemer2017,
  author    = {Schmidt, Bernd and Riemer, Martin},
  title     = {Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols},
  series = {Journal of Heterocyclic Chemistry},
  volume    = {54},
  journal   = {Journal of Heterocyclic Chemistry},
  number    = {2},
  publisher = {Wiley},
  address   = {Hoboken},
  issn      = {0022-152X},
  doi       = {10.1002/jhet.2704},
  pages     = {1287 -- 1297},
  year      = {2017},
  abstract  = {ortho-Aryl phenols, synthesized via protecting group free Suzuki-Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C-H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)(2) without additional ligands.},
  language  = {en}
}
@article{LoodTikkKruegeretal.2022,
  author    = {Lood, Kajsa and Tikk, Triin and Kr{\"u}ger, Mandy and Schmidt, Bernd},
  title     = {Methylene capping facilitates cross-metathesis reactions of enals},
  series = {The journal of organic chemistry},
  volume    = {87},
  journal   = {The journal of organic chemistry},
  number    = {5},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.1c02851},
  pages     = {3079 -- 3088},
  year      = {2022},
  abstract  = {Four combinations of type-I olefins isoeugenol and 4-hydroxy-3-methoxystyrene with type-II olefins acrolein and crotonaldehyde were investigated in cross-metathesis (CM) reactions. While both type-I olefins are suitable CM partners for this transformation, we observed synthetically useful conversions only with type-II olefin crotonaldehyde. For economic reasons, isoeugenol, a cheap xylochemical available from renewable lignocellulose or from clove oil, is the preferred type-I CM partner. Nearly quantitative conversions to coniferyl aldehyde by the CM reaction of isoeugenol and crotonaldehyde can be obtained at ambient temperature without a solvent or at high substrate concentrations of 2 mol.L-1 with the second-generation Hoveyda-Grubbs catalyst. Under these conditions, the ratio of reactants can be reduced to 1:1.5 and catalyst loadings as low as 0.25 mol \% are possible. The high reactivity of the isoeugenol/crotonaldehyde combination in olefin metathesis reactions was demonstrated by a short synthesis of the natural product 7-methoxywutaifuranal, which was obtained from isoeugenol in a 44\% yield over five steps. We suggest that the superior performance of crotonaldehyde in the CM reactions investigated can be rationalized by "methylene capping", i.e., the steric stabilization of the propagating Ru-alkylidene species.},
  language  = {en}
}
@article{KrauseSperlichSchmidt2021,
  author    = {Krause, Andreas and Sperlich, Eric and Schmidt, Bernd},
  title     = {Matsuda-Heck arylation of itaconates},
  series = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry},
  volume    = {19},
  journal   = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry},
  number    = {19},
  publisher = {Royal Society of Chemistry},
  address   = {Cambridge},
  issn      = {1477-0520},
  doi       = {10.1039/d1ob00392e},
  pages     = {4292 -- 4302},
  year      = {2021},
  abstract  = {Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in one or two steps to benzazepine-2-ones.},
  language  = {en}
}
@article{OtteSchmidt2019,
  author    = {Otte, Fabian and Schmidt, Bernd},
  title     = {Matsuda-Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C-Glycosides},
  series = {The journal of organic chemistry},
  volume    = {84},
  journal   = {The journal of organic chemistry},
  number    = {22},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.9b02410},
  pages     = {14816 -- 14829},
  year      = {2019},
  abstract  = {The methoxymethyl-protected glycal L-amicetal, synthesized de novo from L-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an a-configured 6-desoxy-gliflozin derivative.},
  language  = {en}
}
@article{RiemerShipmanWessigetal.2019,
  author    = {Riemer, Nastja and Shipman, Michael and Wessig, Pablo and Schmidt, Bernd},
  title     = {Iterative arylation of itaconimides with diazonium salts through electrophilic palladium catalysis},
  series = {The journal of organic chemistry},
  volume    = {84},
  journal   = {The journal of organic chemistry},
  number    = {9},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.9b00627},
  pages     = {5732 -- 5746},
  year      = {2019},
  abstract  = {N-Arylitaconimides, accessible from maleic anhydride, anilines, and paraformaldehyde, react with arene diazonium salts in Pd-catalyzed Matsuda-Heck arylation to the pharmacologically relevant E-configured 3-arylmethylidene pyrrolidine-2,5-diones (also known as arylmethylidene succinimides) through exo-selective beta-H-elimination. The coupling proceeds at ambient temperature with the simple and easy-to-handle precatalyst Pd-II-acetate under ligandand base-free conditions. Notable features are high isolated yields, regio- and stereoselectivities, and short reaction times. In a comparative investigation, aryl iodides, bromides, and triflates were shown to be inferior coupling reagents in this reaction. The 3-arylmethylidene pyrrolidine-2,5-diones undergo second Matsuda-Heck coupling, which proceeds via endo-selective beta-H-elimination to give diarylmethyl-substituted maleimides as coupling products. These products can also be accessed in one flask by sequential addition of different arene diazonium salts to the starting itaconimide. The potential of 3-arylmethylidene succinimides as photoswitches was tested. Upon irradiation of the E-isomer at 300 nm, partial isomerization to the Z-isomer (E/Z = 65:35 in the photostationary state) was observed. The isomerization was found to be nearly completely reversible by irradiating the mixture at 400 nm.},
  language  = {en}
}
@article{SperlichKellingKwesigaetal.2022,
  author    = {Sperlich, Eric and Kelling, Alexandra and Kwesiga, George and Schmidt, Bernd},
  title     = {Intermolecular interactions in the solid-state structures of isoflavones},
  series = {CrystEngComm / The Royal Society of Chemistry},
  volume    = {24},
  journal   = {CrystEngComm / The Royal Society of Chemistry},
  number    = {26},
  publisher = {Royal Society of Chemistry},
  address   = {London},
  issn      = {1466-8033},
  doi       = {10.1039/d2ce00169a},
  pages     = {4731 -- 4739},
  year      = {2022},
  abstract  = {The molecular structures of three closely related isoflavones have been determined by single crystal X-ray diffraction and have been analysed by geometry matching with the CSD, Hirshfeld surface analysis and analysis of stacking interactions with the Aromatic Analyser program (CSD). The formation of the supramolecular structure by non-covalent interactions was studied and substantial differences in the macroscopic properties e.g., the solubility, were correlated with hydrogen bonding and pi-stacking interactions. Moreover, a correlation between the supramolecular structure, the torsion angle (between benzopyran group and aryl group), and macroscopic properties was determined in the three compounds.},
  language  = {en}
}
@article{KarrasDabrowskiPohletal.2018,
  author    = {Karras, Manfred and Dabrowski, Michal and Pohl, Radek and Rybacek, Jiri and Vacek, Jaroslav and Bednarova, Lucie and Grela, Karol and Stary, Ivo and Stara, Irena G. and Schmidt, Bernd},
  title     = {Helicenes as Chirality-Inducing Groups in Transition-Metal Catalysis},
  series = {Chemistry - a European journal},
  volume    = {24},
  journal   = {Chemistry - a European journal},
  number    = {43},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {0947-6539},
  doi       = {10.1002/chem.201802786},
  pages     = {10994 -- 10998},
  year      = {2018},
  abstract  = {Helical chirality is a novel enantioselectivity-inducing property in transition-metal-catalyzed transformations. The principle is illustrated herein for the example of asymmetric olefin metathesis. This work reports the synthesis of the first helically chiral Ru-NHC alkylidene complex from an aminohelicene-derived imidazolium salt, which was ligated to the first generation Hoveyda-Grubbs catalyst. Kinetic data were acquired for benchmark test reactions and compared to an achiral catalyst. The helically chiral Ru-catalyst was evaluated in asymmetric ring-closing metathesis (RCM) and ring-opening metathesis-cross-metathesis (ROM/CM) reactions, which proceeded with promising levels of enantioselectivity. Extensive NMR-spectroscopic investigations and a DFT geometry optimization were performed. These results led to a topographic steric map and calculation of percent-buried-volume values for each quadrant around the metal center.},
  language  = {en}
}
@book{BuddrusSchmidt2015,
  author    = {Buddrus, Joachim and Schmidt, Bernd},
  title     = {Grundlagen der organischen Chemie},
  edition   = {5., {\"u}berarb. und aktualisierte Aufl.},
  publisher = {de Gruyter},
  address   = {Berlin},
  isbn      = {978-3-11-030559-3},
  publisher      = {Universit{\"a}t Potsdam},
  pages     = {946},
  year      = {2015},
  language  = {de}
}
@article{SchultzeSchmidt2019,
  author    = {Schultze, Christiane and Schmidt, Bernd},
  title     = {Functionalized Benzofurans via Microwave-Promoted Tandem Claisen-Rearrangement/5-endo-dig Cyclization},
  series = {Journal of heterocyclic chemistry},
  volume    = {56},
  journal   = {Journal of heterocyclic chemistry},
  number    = {9},
  publisher = {Wiley},
  address   = {Hoboken},
  issn      = {0022-152X},
  doi       = {10.1002/jhet.3671},
  pages     = {2619 -- 2629},
  year      = {2019},
  abstract  = {Ortho-allyloxy alkinyl benzenes undergo, upon microwave irradiation in dimethylformamide, a tandem sequence of Claisen-rearrangement and 5-endo-dig cyclization to furnish 7-allyl-substituted benzofurans. With terminal alkynes, chroman-4-ones and enaminoketones become the main products. A mechanistic proposal for this observation relies on a reaction of the starting material with the solvent dimethylformamide under the microwave conditions.},
  language  = {en}
}
@article{AriasFeuerbachSchmidtetal.2018,
  author    = {Arias, Hugo R. and Feuerbach, Dominik and Schmidt, Bernd and Heydenreich, Matthias and Paz, Cristian and Ortells, Marcelo O.},
  title     = {Drimane Sesquiterpenoids Noncompetitively Inhibit Human alpha 4 beta 2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human alpha 3 beta 4 and alpha 7 Subtypes},
  series = {Journal of natural products},
  volume    = {81},
  journal   = {Journal of natural products},
  number    = {4},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0163-3864},
  doi       = {10.1021/acs.jnatprod.7b00893},
  pages     = {811 -- 817},
  year      = {2018},
  abstract  = {The drimane sesquiterpenoids drimenin, cinnamolide, dendocarbin A, and polygodial were purified from the Canelo tree (Drimys winteri) and chemically characterized by spectroscopic methods. The pharmacological activity of these natural compounds were determined on hα4β2, hα3β4, and hα7 nicotinic acetylcholine receptors (AChRs) by Ca2+ influx measurements. The results established that drimane sesquiterpenoids inhibit AChRs with the following selectivity: hα4β2 > hα3β4 > hα7. In the case of hα4β2 AChRs, the following potency rank order was determined (IC50's in μM): drimenin (0.97 ± 0.35) > cinnamolide (1.57 ± 0.36) > polygodial (62.5 ± 19.9) ≫ dendocarbin A (no activity). To determine putative structural features underlying the differences in inhibitory potency at hα4β2 AChRs, additional structure-activity relationship and molecular docking experiments were performed. The Ca2+ influx and structural results supported a noncompetitive mechanism of inhibition, where drimenin interacted with luminal and nonluminal (TMD-β2 intrasubunit) sites. The structure-activity relationship results, i.e., the lower the ligand polarity, the higher the inhibitory potency, supported the nonluminal interaction. Ligand binding to both sites might inhibit the hα4β2 AChR by a cooperative mechanism, as shown experimentally (nH > 1). Drimenin could be used as a molecular scaffold for the development of more potent inhibitors with higher selectivity for the hα4β2 AChR.},
  language  = {en}
}
@article{HermannsSchmidt2018,
  author    = {Hermanns, Jolanda and Schmidt, Bernd},
  title     = {Developing and Applying Stepped Supporting Tools in Organic Chemistry To Promote Students' Self-Regulated Learning},
  series = {Journal of chemical education},
  volume    = {96},
  journal   = {Journal of chemical education},
  number    = {1},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0021-9584},
  doi       = {10.1021/acs.jchemed.8b00565},
  pages     = {47 -- 52},
  year      = {2018},
  abstract  = {Stepped supporting tools were developed and used in the university seminar Organic Chemistry taken by nonmajor chemistry students, which supported self-regulated learning. These supporting tools were also used for accompanying homework, which included a QR code that led to additional supporting tools. The application of stepped supporting tools in the seminars was evaluated by a four-item Likert scale. The students assessed the tools as a helpful instrument for solving tasks in chemistry.},
  language  = {en}
}
@article{HolecRybačekVaceketal.2019,
  author    = {Holec, Jan and Ryb{\´a}ček, Jiř{\´i} and Vacek, Jaroslav and Karras, Manfred and Bedn{\´a}rov{\´a}, Lucie and Budesinsky, Milos and Slusna, Michaela and Holy, Petr and Schmidt, Bernd and Star{\´a}, Irena G. and Star{\´y}, Ivo},
  title     = {Chirality-Controlled Self-Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir-Blodgett Thin Films},
  series = {Chemistry - a European journal},
  volume    = {25},
  journal   = {Chemistry - a European journal},
  number    = {49},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {0947-6539},
  doi       = {10.1002/chem.201901695},
  pages     = {11494 -- 11502},
  year      = {2019},
  abstract  = {Racemic and highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo[6]helicene were prepared. The Langmuir layers of these helicenes were formed at the air-water interface and transferred onto solid substrates to afford Langmuir-Blodgett films, which were then studied by ambient atomic force microscopy and (chir)optical spectroscopy. Significant differences were found in the behaviour of the Langmuir layers as well as in the morphology, UV/Vis, electronic circular dichroism (ECD), and fluorescence spectra of the Langmuir-Blodgett thin films depending on the molecular chirality and nature of the polar group. The experimental results were supported by molecular dynamics simulations.},
  language  = {en}
}
@article{SchmidtPetersenBraun2018,
  author    = {Schmidt, Bernd and Petersen, Monib H. and Braun, Diana},
  title     = {Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C-2-Symmetric Building Block Using Olefin Metathesis Reactions},
  series = {The journal of organic chemistry},
  volume    = {83},
  journal   = {The journal of organic chemistry},
  number    = {3},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.7b02944},
  pages     = {1627 -- 1633},
  year      = {2018},
  abstract  = {(5R,6S)-6-Acetoxy-5-hexadecanolide (MOP) is the oviposition pheromone of the mosquito Cx. quinquefasciatus, a vector of pathogens causing a variety of tropical diseases. We describe and evaluate herein three syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C-2-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in situ conversion of a Ru-carbene to a Ru-hydride.},
  language  = {en}
}
@article{KarrasHolecBednarovaetal.2018,
  author    = {Karras, Manfred and Holec, Jan and Bednarova, Lucie and Pohl, Radek and Schmidt, Bernd and Stara, Irena G. and Stary, Ivo},
  title     = {Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films},
  series = {The journal of organic chemistry},
  volume    = {83},
  journal   = {The journal of organic chemistry},
  number    = {10},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/acs.joc.8b00538},
  pages     = {5523 -- 5538},
  year      = {2018},
  abstract  = {Alternative ways of preparing nonracemic 2-amino[6]helicene derivatives were explored. The enantioselective [2 + 2 + 2] cycloisomerization of a nonchiral triyne under Ni(cod)(2)/(R)-QUINAP catalysis delivered the enantioenriched (+)-(P)-2-aminodibenzo[6]helicene derivative in 67\% ee. An ultimate "point-to-helical" chirality transfer was observed in the cyclization of enantiopure triynes mediated by Ni(CO)(2)(PPh3)(2) affording (-)-(M)- or (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amine in >99\% ee as well as its benzoderivative in >99\% ee. The latter mode of stereocontrol was inefficient for a 2-aminobenzo[6]helicene congener with an embedded five-membered ring. The rac-, (-)-(M)-, and (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amines formed Langmuir monolayers at the air water interface featuring practically identical surface pressure vs mean molecular area isotherms. The corresponding Langmuir-Blodgett films on quartz or silicon substrates were characterized by UV vis/ECD spectroscopy and AFM microscopy, respectively.},
  language  = {en}
}
@article{NguyenLeeAudoerschetal.2018,
  author    = {Nguyen, Hiep N. and Lee, Hyeunjoo and Aud{\"o}rsch, Stephan and Reznichenko, Alexander L. and Nawara-Hultzsch, Agnieszka J. and Schmidt, Bernd and Hultzsch, Kai C.},
  title     = {Asymmetric Intra- and Intermolecular Hydroamination Catalyzed by 3,3′-Bis(trisarylsilyl)- and 3,3′-Bis(arylalkylsilyl)-Substituted Binaphtholate Rare-Earth-Metal Complexes},
  series = {Organometallics},
  volume    = {37},
  journal   = {Organometallics},
  number    = {23},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0276-7333},
  doi       = {10.1021/acs.organomet.8b00510},
  pages     = {4358 -- 4379},
  year      = {2018},
  abstract  = {The series of novel 3,3′-bis(trisarylsilyl)- and 3,3′-bis(arylalkylsilyl)-substituted binaphtholate rare-earth-metal complexes 2a-i (SiR3 = Si(o-biphenylene)Ph (a), SiCyPh2 (b), Si-t-BuPh2 (c), Si(i-Pr)3 (d), SiCy2Ph (e), Si(2-tolyl)Ph2 (f), Si(4-t-Bu-C6H4)3 (g), Si(4-MeO-C6H4)Ph2 (h), SiBnPh2 (i)) have been prepared via arene elimination from [Ln(o-C6H4CH2NMe2)3] (Ln = Y, Lu) and the corresponding 3,3′-bis(silyl)-substituted binaphthol. The complexes exhibit high catalytic activity in the hydroamination/cyclization of aminoalkenes, with activities exceeding 1000 h-1 for (R)-2f-Ln, (R)-2g-Ln, and (R)-2h-Ln in the cyclization of 2,2-diphenylpent-4-enylamine (3a) at 25 °C, while the rigid dibenzosilole-substituted complexes (R)-2a-Ln and the triisopropylsilyl-substituted complexes (R)-2d-Ln exhibited the lowest activity in the range of 150-270 h-1. Catalysts (R)-2b-Lu, (R)-2c-Lu, (R)-2f-Lu, and (R)-2i-Lu provide the highest selectivities for the majority of the substrates, while the yttrium congeners are usually less selective. The highest enantioselectivities of 96\% ee were observed using (R)-2a-Lu and (R)-2c-Lu in the cyclization of (4E)-2,2,5-triphenylpent-4-enylamine (9). The reactions show apparently zero-order rate dependence on substrate concentration and first-order rate dependence on catalyst concentration, with some reactions exhibiting a slightly accelerated rate at high conversion due to a shift in the equilibrium between a less active, higher coordinate catalyst species in favor of a more active, lower coordinate species as a result of weaker binding of the hydroamination product in comparison to the aminoalkene substrate. The shift in equilibrium from the higher to the lower coordinate species is also entropically favored at elevated temperatures, which results in an unusual increase in selectivity in the cyclization of 2,2-dimethylpent-4-enylamine (3d), presumably due to a higher selectivity of the lower coordinate catalyst species. All binaphtholate yttrium complexes, except (R)-2a-Y, are catalytically active in the intermolecular hydroamination of benzylamines with terminal alkenes. The highest selectivity of 66\% ee was observed for the reaction of benzylamine with 4-phenyl-1-butene using (R)-2h-Y at 110 °C.},
  language  = {en}
}
@article{OloyaNamukobeHeydenreichetal.2021,
  author    = {Oloya, Benson and Namukobe, Jane and Heydenreich, Matthias and Ssengooba, Willy and Schmidt, Bernd and Byamukama, Robert},
  title     = {Antimycobacterial activity of the extract and isolated compounds from the stem bark of Zanthoxylum leprieurii Guill. and Perr.},
  series = {Natural product communications : an international journal for communications and reviews},
  volume    = {16},
  journal   = {Natural product communications : an international journal for communications and reviews},
  number    = {8},
  publisher = {Sage Publ.},
  address   = {Thousand Oaks},
  issn      = {1934-578X},
  doi       = {10.1177/1934578X211035851},
  pages     = {8},
  year      = {2021},
  abstract  = {Zanthoxylum leprieurii Guill. and Perr. (Rutaceae) stem bark is used locally in Uganda for treating tuberculosis (TB) and cough-related infections. Lupeol (1), sesamin (2), trans-fagaramide (3), arnottianamide (4), (S)-marmesinin (5), and hesperidin (6) were isolated from the chloroform/methanol (1:1) extract of Z. leprieurii stem bark. Their structures were elucidated using spectroscopic techniques and by comparison with literature data. Furthermore, the extract and isolated compounds were subjected to antimycobacterial activity. The extract exhibited moderate activity against the susceptible (H(37)Rv) TB strain, but weak activity against the multidrug resistant (MDR)-TB strain with minimum inhibitory concentrations (MICs) of 586.0 and 1172.0 mu g/mL, respectively. Compound 3 (trans-fagaramide) showed significant antimycobacterial activity against the susceptible (H(37)Rv) TB strain (MIC 6 mu g/mL), but moderate activity against the MDR-TB strain (MIC 12.2 mu g/mL). Compounds 2, 5, 6, and 1 showed moderate activities against the susceptible (H(37)Rv) strain (MIC 12.2-98.0 mu g/mL) and moderate to weak activities against the MDR-TB strain (MIC 24.4-195.0 mu g/mL). This study reports for the first time the isolation of compounds 1 to 6 from the stem bark of Z leprieurii. trans-Fagaramide (3) may present a vital template in pursuit of novel and highly effective TB drugs.},
  language  = {en}
}
@article{SchultzeFossSchmidt2020,
  author    = {Schultze, Christiane and Foß, Stefan and Schmidt, Bernd},
  title     = {8-Prenylflavanones through microwave promoted tandem claisen rearrangement/6-endo-trig cyclization and cross metathesis},
  series = {European journal of organic chemistry},
  volume    = {2020},
  journal   = {European journal of organic chemistry},
  number    = {47},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.202001378},
  pages     = {7373 -- 7384},
  year      = {2020},
  abstract  = {Prenylated flavanones were obtained from ortho-allyloxy chalcones through a one-pot sequence of Claisen rearrangement and 6-endo-trig cyclization, followed by olefin cross metathesis of the intermediate allyl flavanones with 2-methyl-2-butene. The synthetic utility of this route is illustrated for the synthesis of several naturally occurring prenyl flavanones.},
  language  = {en}
}