Vanadium-Catalyzed Asymmetric Oxidation of α-Hydroxy Esters Using Molecular Oxygen as Stoichiometric Oxidant

Alexander T. Radosevich; Christine Musich; Dean Toste

doi:10.1021/ja0433424

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Vanadium-Catalyzed Asymmetric Oxidation of α-Hydroxy Esters Using Molecular Oxygen as Stoichiometric Oxidant

Article 2005 en

Authors

AR
Alexander T. Radosevich
CM
Christine Musich
Dean Toste
University of California, Berkeley

Abstract

1 min read

A vanadium-catalyzed method for the oxidative kinetic resolution of alpha-hydroxyesters, using oxygen as the terminal oxidant, is described. The catalyst is generated in situ from vanadium(V) tri-iso-propoxyoxide in combination with a tridentate ligand derived from 3,5-di-tert-butylsalicylaldehyde and (S)-tert-leucinol. The reaction allows for the enantioselective synthesis of both aromatic and aliphatic secondary alcohols, including those containing olefins and alkynes.

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