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Kinetic Resolution of α‐Hydroxy‐Substituted Oxime Ethers by Enantioselective Cu−H‐Catalyzed Si−O Coupling
Author(s) -
Dong Xichang,
Kita Yuji,
Oestreich Martin
Publication year - 2018
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.201802947
Subject(s) - enantioselective synthesis , kinetic resolution , oxime , catalysis , chemistry , selectivity , ether , silyl ether , silylation , alcohol , organic chemistry , combinatorial chemistry , medicinal chemistry
A catalyst‐controlled enantioselective alcohol silylation by Cu−H‐catalyzed dehydrogenative Si−O coupling of hydroxy groups α to an oxime ether and simple hydrosilanes is reported. The selectivity factors reached in this kinetic resolution are generally high ( s ≈50), and these reactions thereby provide reliable access to highly enantioenriched α‐hydroxy‐substituted oxime ethers. The synthetic usefulness of these compounds is also demonstrated.