@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{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{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}
}
@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{SchmidtKunz2012,
  author    = {Schmidt, Bernd and Kunz, Oliver},
  title     = {One-Flask tethered ring closing Metathesis-Electrocyclic ring opening for the highly stereoselective synthesis of conjugated Z/E-Dienes},
  series = {European journal of organic chemistry},
  journal   = {European journal of organic chemistry},
  number    = {5},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.201101497},
  pages     = {1008 -- 1018},
  year      = {2012},
  abstract  = {A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised.},
  language  = {en}
}