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Catalytic Dynamic Kinetic Resolutions with N‐Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β‐Lactones
Author(s) -
Cohen Daniel T.,
Eichman Chad C.,
Phillips Eric M.,
Zarefsky Emily R.,
Scheidt Karl A.
Publication year - 2012
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.201203382
Subject(s) - catalysis , kinetic resolution , chemistry , kinetic energy , enantioselective synthesis , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , physics , quantum mechanics
New DKR type : An N‐heterocyclic carbene (NHC)‐catalyzed dynamic kinetic resolution of racemic α‐substituted β‐keto esters has been developed. This method relies on the epimerization of an NHC‐enol intermediate before subsequent aldol/acylation events. Highly substituted β‐lactones are produced in good yield with good to excellent selectivities (see scheme).