@article{SchmidtGeissler2011, author = {Schmidt, Bernd and Geissler, Diana}, title = {Olefin-Metathesis-Based Synthesis of Furans by an RCM/Deprotonation/Phosphorylation Sequence and Their Diels-Alder Reactions}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {35}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201101078}, pages = {7140 -- 7147}, year = {2011}, abstract = {Butenolides, obtained by ring-closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent DielsAlder reaction and acid-catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes.}, language = {en} } @article{SchmidtGeissler2011, author = {Schmidt, Bernd and Geissler, Diana}, title = {Ru- and Pd-Catalysed Synthesis of 2-Arylfurans by One-Flask Heck Arylation/Oxidation}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {25}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201100549}, pages = {4814 -- 4822}, year = {2011}, abstract = {2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disub-stituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.}, language = {en} } @article{SchmidtHauke2014, author = {Schmidt, Bernd and Hauke, Sylvia}, title = {Metathesis-Based de novo synthesis of noviose}, series = {European journal of organic chemistry}, volume = {2014}, journal = {European journal of organic chemistry}, number = {9}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201301615}, pages = {1951 -- 1960}, year = {2014}, abstract = {The rare carbohydrate L-(+)-noviose was synthesized from enantiomerically pure L-lactate. The configuration at C-4 was established by diastereoselective nucleophilic addition to an in-situ-generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring-closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM-allylic-oxidation sequences.}, language = {en} } @article{SchmidtRiemerSchilde2015, author = {Schmidt, Bernd and Riemer, Martin and Schilde, Uwe}, title = {Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {34}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201501151}, pages = {7602 -- 7611}, year = {2015}, abstract = {Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.}, language = {en} } @article{SchmidtSchultze2018, author = {Schmidt, Bernd and Schultze, Christiane}, title = {A one-pot synthesis of pyranocoumarins through microwave-promoted propargyl claisen rearrangement/wittig olefination}, series = {European journal of organic chemistry}, volume = {2018}, journal = {European journal of organic chemistry}, number = {2}, publisher = {Wiley-VCH Verl.}, address = {Weinheim}, issn = {1434-193X}, pages = {223 -- 227}, year = {2018}, abstract = {The reaction between propargyl ethers of hydroxybenzaldehydes and the ylide ethyl (triphenylphosphoranylidene)acetate was carried out under microwave irradiation to regioselectively afford angular pyranocoumarins. The chromene and coumarin heterocyclic scaffolds were simultaneously formed in the same synthetic step without changing the reaction conditions. The natural products seselin, braylin, and dipetalolactone were among the products synthesized by this method.}, language = {en} } @article{SchmidtStaudeKellingetal.2011, author = {Schmidt, Bernd and Staude, Lucia and Kelling, Alexandra and Schilde, Uwe}, title = {A Cross-Metathesis-Conjugate addition route to enantiopure gamma-Butyrolactams and gamma-Lactones from a C-2-Symmetric Precursor}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {9}, publisher = {Wiley-Blackwell}, address = {Malden}, issn = {1434-193X}, doi = {10.1002/ejoc.201001528}, pages = {1721 -- 1727}, year = {2011}, abstract = {A protected derivative of (3R, 4R)-hexa-1,5-diene-3,4-diol, a conveniently accessible C-2-symmetric building block, undergoes single or double cross metathesis with methyl acryl-ate. The cross metathesis products are amenable to stereoselective conjugate addition reactions and can be converted into either gamma-butyrolactones or gamma-lactams.}, language = {en} }