Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions

• Main Authors: Wu, Xingxing, Liu, Bin, Zhang, Yuexia, Jeret, Martin, Wang, Honglin, Zheng, Pengcheng, Yang, Song, Song, Bao-An, Chi, Yonggui Robin
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2017
• Subjects: Cycloaddition; Heterocycles
• Online Access: https://hdl.handle.net/10356/85620; http://hdl.handle.net/10220/43780
• Institution: Nanyang Technological University

An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives.