Oxidation of Catecholboron Enolates with TEMPO

Oxidation of Catecholboron Enolates with TEMPO

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...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (33), p.6037-6040
Hauptverfasser: Pouliot, Martin, Renaud, Philippe, Schenk, Kurt, Studer, Armido, Vogler, Thomas
Format: Artikel
Sprache:eng
Schlagworte:
alkoxyamines
Boron - chemistry
boron enolates
Catechols - chemistry
Cyclic N-Oxides - chemistry
enolyl radicals
Ketones - chemistry
nitroxides
oxidation
Oxidation-Reduction
Stereoisomerism
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Beschreibung
Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902242