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NHC Organocatalytic Formal LUMO Activation of α,β‐Unsaturated Esters for Reaction with Enamides
Author(s) -
Cheng Jiajia,
Huang Zhijian,
Chi Yonggui Robin
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303247
Subject(s) - nucleophile , chemistry , carbene , combinatorial chemistry , michael reaction , optically active , acceptor , organic chemistry , computer science , catalysis , physics , condensed matter physics
An effective wake‐up call : Stable α,β‐unsaturated esters were activated by the addition of a chiral N‐heterocyclic carbene (NHC) organocatalyst, and the resulting reactive Michael acceptor intermediates reacted with enamide nucleophiles to furnish optically pure products (see scheme; Ts= p ‐toluenesulfonyl). These products can be converted readily into bioactive δ‐lactams, piperidines, and their derivatives.