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- Title
N-Heterocyclic Carbene Catalyzed Cyclocondensation of a,b- Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives.
- Authors
Chen, Xiang‐Yu; Gao, Zhong‐Hua; Song, Chun‐Yu; Zhang, Chun‐Lin; Wang, Zhi‐Xiang; Ye, Song
- Abstract
The catalytic cyclocondensation of in situ activated α,β-unsaturated carboxylic acids was developed. N-heterocyclic carbenes efficiently catalyzed the generation of a,bunsaturated acyl azolium intermediates from a,b-unsaturated carboxylic acids via in situ generated mixed anhydrides for the enantioselective [3+2] and [3+3] cyclocondensation with aamino ketones and alkyl(aryl)imines, respectively. The corresponding pyrrolidinones and dihydropyridinones were isolated in good yields with high to excellent enantioselectivities.
- Subjects
CARBENES; CONDENSATION; CARBOXYLIC acids; ENANTIOSELECTIVE catalysis; PYRROLIDINONES; PYRIDONE derivatives
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 43, p11611
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201407469