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Oxidation of Catecholboron Enolates with TEMPO
Author(s) -
Pouliot Martin,
Renaud Philippe,
Schenk Kurt,
Studer Armido,
Vogler Thomas
Publication year - 2009
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.200902242
Subject(s) - computer science
Persistent radical meets enolates : Catecholboron ketone enolates are oxidized efficiently under mild conditions by treatment with the persistent TEMPO radical. Catecholboron enolates are readily prepared by 1,4‐reduction of α,β‐unsaturated ketones or by transmetalation of silyl enol ethers and zinc enolates with chlorocatecholboranes. Enolate formation and oxidation can be performed as a one‐pot process with high regio‐ and stereoselectivity.