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Title: Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions
Authors: Wu, Xingxing
Liu, Bin
Zhang, Yuexia
Jeret, Martin
Wang, Honglin
Zheng, Pengcheng
Yang, Song
Song, Bao-An
Chi, Yonggui Robin
Keywords: Cycloaddition
Issue Date: 2016
Source: Wu, X., Liu, B., Zhang, Y., Jeret, M., Wang, H., Zheng, P., et al. (2016). Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions. Angewandte Chemie International Edition, 55(40), 12280-12284.
Series/Report no.: Angewandte Chemie International Edition
Abstract: 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.
ISSN: 1433-7851
DOI: 10.1002/anie.201606571
Rights: © 2016 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim
Fulltext Permission: none
Fulltext Availability: No Fulltext
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