期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 40, 页码 11800-11803出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505161
关键词
enantioselectivity; natural products; olefination; palladium; total synthesis
资金
- Resnick Sustainability Institute at Caltech
- NIH [R01M080269, 5R01M031332-27]
- Gordon and Betty Moore Foundation
- Caltech Center for Catalysis and Chemical Synthesis
- Caltech
The direct alpha-vinylation of carbonyl compounds to form a quaternary stereocenter is a challenging transformation. It was discovered that delta-oxocarboxylic acids can serve as masked vinyl compounds and be unveiled by palladium-catalyzed decarbonylative dehydration. The carboxylic acids are readily available through enantioselective acrylate addition or asymmetric allylic alkylation. A variety of alpha-vinyl quaternary carbonyl compounds are obtained in good yields, and an application in the first enantioselective total synthesis of (-)-aspewentins A, B, and C is demonstrated.
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