期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 39, 页码 17256-17260出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007639
关键词
1; 4-addition reactions; boronic acids; cooperative catalysis; enantioselectivity; carboxylic acids
资金
- JSPS KAKENHI [15H05755, 15H06266, 17K14484, 15H05810]
- Toyoaki Scholarship Foundation
- MEXT, Japan
- Society of Iodine Science
- Grants-in-Aid for Scientific Research [17K14484, 15H06266, 15H05810] Funding Source: KAKEN
An enantioselective 1,4-addition of alpha,beta-unsaturated carboxylic acids with cycloalkanones has been developed by using chiral amine-boronic acid cooperative catalysts. In the presence of a chiral amine and boronic acid, cycloalkanones and carboxylic acids are activated as chiral enamines and mixed anhydrides, respectively. The corresponding 1,4-adducts are obtained in high yield with high enantioselectivity. Furthermore, subsequent oxylactonization of the 1,4-adducts gives spirolactones with high diastereoselectivity.
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