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Stereoselective Formation of Fully Substituted Ketone Enolates
Author(s) -
Haimov Elvira,
Nairoukh Zackaria,
Shterenberg Alexander,
Berkovitz Tiran,
Jamison Timothy F.,
Marek Ilan
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601883
Subject(s) - stereocenter , enantioselective synthesis , ketone , aldol reaction , chemistry , diastereomer , metalation , quaternary carbon , enol , stereoselectivity , stereochemistry , organic chemistry , catalysis
Abstract The application of stereochemically defined acyclic fully substituted enolates of ketones to the enantioselective synthesis of quaternary carbon stereocenters would be highly valuable. Herein, we describe an approach leading to the formation of several new stereogenic centers through a combined metalation–addition of a carbonyl–carbamoyl transfer to reveal in situ stereodefined α,α‐disubstituted enolates of ketone as a single stereoisomer. This approach could produce a series of aldol and Mannich products from enol carbamate with excellent diastereomeric ratios.