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- Title
N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β- 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 α,β-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; HETEROCYCLIC compounds; CARBOXYLIC acids; PYRROLIDINONES; PYRIDONE derivatives; PYRIDONE synthesis
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 43, p11795
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201407469