N‐Heterocyclic Carbene Catalyzed Cyclocondensation of α, β‐Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives1. Issue 43 (9th September 2014)

• Record Type: Journal Article
• Authors: Chen, Xiang‐Yu; Gao, Zhong‐Hua; Song, Chun‐Yu; Zhang, Chun‐Lin; Wang, Zhi‐Xiang; Ye, Song
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 43(2014)
• Page Start: 11611
• Page End: 11615
• Publication Date: 2014-09-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201407469
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The catalytic cyclocondensation of in situ activated α, β‐unsaturated carboxylic acids was developed. N‐heterocyclic carbenes efficiently catalyzed the generation of α, β‐unsaturated 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 α‐amino ketones and alkyl(aryl)imines, respectively. The corresponding pyrrolidinones and dihydropyridinones were isolated in good yields with high to excellent enantioselectivities.</p> </abstract>