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Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters
Author(s) -
Nairoukh Zackaria,
Marek Ilan
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.201507209
Subject(s) - stereocenter , aldol reaction , ketene , silylation , chemistry , stereoselectivity , quaternary carbon , organic chemistry , enantioselective synthesis , stereochemistry , catalysis
Abstract The regio‐ and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation–oxidation–silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.