Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 42, Pages 18709-18716Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008365
Keywords
catalysis; computational chemistry; density functional calculations; Michael additions; natural products
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Funding
- Studienstiftung des deutschen Volkes
- Universitat zu Koln
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [GRK2158]
- Heinrich-Heine-Universitat Dusseldorf
- German Federal Ministry for Economic Affairs and Energy (ZIM Kooperationsprojekt) [KF3279X01AJ3]
- Forschungszentrum Julich GmbH
- DFG
- Projekt DEAL
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The reactions of alpha,beta-unsaturated delta-lactones with activated dienes such as 1,3-dimethoxy-1-[(trimethylsilyl)oxy]-1,3-butadiene (Brassard's diene) are barely known in literature and show high potential for the synthesis of isocoumarin moieties. An in-depth investigation of this reaction proved a stepwise mechanism via the vinylogous Michael-products. Subsequent cyclisation and oxidation by LHMDS and DDQ, respectively, provided six mellein derivatives (30-84 %) and four angelicoin derivatives (40-78 %) over three steps. DFT-calculations provide insights into the reaction mechanism and support the theory of a stepwise reaction.
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