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Intermolecular Dynamic Kinetic Resolution Cooperatively Catalyzed by an N‐Heterocyclic Carbene and a Lewis Acid
Author(s) -
Wu Zijun,
Li Fangyi,
Wang Jian
Publication year - 2015
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.201410030
Subject(s) - carbene , stereocenter , kinetic resolution , intermolecular force , enantioselective synthesis , chemistry , lewis acids and bases , catalysis , stereoselectivity , stereochemistry , combinatorial chemistry , organic chemistry , molecule
Abstract The ubiquitous structure of δ‐lactones makes the development of new methods for their enantioselective and stereoselective synthesis an important ongoing challenge. The intermolecular dynamic kinetic resolution (DKR) of β‐halo‐α‐ketoesters cooperatively catalyzed by an N‐heterocyclic carbene and a Lewis acid generates two contiguous stereocenters with remarkable diastereoselectivity through an oxidation/lactonization sequence.