Synthesis 2018; 50(14): 2721-2726
DOI: 10.1055/s-0037-1609966
paper
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

Alejandro Gómez-Palomino
Departament de Química Inorgànica i Orgànica, Secció de Química Orgànica, and Institut de Biomedicina (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1–11, 08028 Barcelona, Catalonia, Spain   Email: felix.urpi@ub.edu   Email: pedro.romea@ub.edu
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Departament de Química Inorgànica i Orgànica, Secció de Química Orgànica, and Institut de Biomedicina (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1–11, 08028 Barcelona, Catalonia, Spain   Email: felix.urpi@ub.edu   Email: pedro.romea@ub.edu
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Departament de Química Inorgànica i Orgànica, Secció de Química Orgànica, and Institut de Biomedicina (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1–11, 08028 Barcelona, Catalonia, Spain   Email: felix.urpi@ub.edu   Email: pedro.romea@ub.edu
› Author Affiliations
Financial support from the Spanish Ministerio de Economía y Competitividad (Grant No. CTQ2015-65759-P) and the Generalitat de Catalunya (2014 SGR586 and 2017SGR 271) as well as a doctorate studentship to A.G.-P. (APIF, Universitat de Barcelona) are acknowledged.
Further Information

Publication History

Received: 13 March 2018

Accepted after revision: 13 April 2018

Publication Date:
29 May 2018 (online)


Abstract

A novel approach to synthesize enantiomerically pure α-hydroxy carboxylic derivatives is reported. A highly stereoselective oxidation of titanium(IV) enolates from chiral N-acyloxazolidinones is performed with oxygen under simple experimental conditions that do not require any reducing steps. The success of this approach depends on the biradical character of titanium(IV) enolates.

Supporting Information

 
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