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Enantioselective Nucleophilic β‐Carbon‐Atom Amination of Enals: Carbene‐Catalyzed Formal [3+2] Reactions
Author(s) -
Wu Xingxing,
Liu Bin,
Zhang Yuexia,
Jeret Martin,
Wang Honglin,
Zheng Pengcheng,
Yang Song,
Song BaoAn,
Chi Yonggui Robin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606571
Subject(s) - enantioselective synthesis , nucleophile , chemistry , amination , carbene , catalysis , carbon fibers , hydrazine (antidepressant) , combinatorial chemistry , organocatalysis , organic chemistry , materials science , composite number , composite material , chromatography
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 β 3 ‐amino‐acid derivatives.