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

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

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 azoliu...

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Bibliographic Details
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
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Institution: Nanyang Technological University
Language: English
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Summary: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.

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