Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

Alejandro Gómez-Palomino; Pedro Romea; Fèlix Urpí

doi:10.1055/s-0037-1609966

Synthesis, Table of Contents

Synthesis 2018; 50(14): 2721-2726
DOI: 10.1055/s-0037-1609966

paper

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

,

Pedro Romea *

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

,

Fèlix Urpí *

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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Abstract

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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.

Key words

stereoselective synthesis - hydroxylation - titanium enolates - chiral auxiliaries - oxygen - radicals

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References

References

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