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

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

A vanadium-catalyzed method for the oxidative kinetic resolution of α-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 (...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2005-02, Vol.127 (4), p.1090-1091
Hauptverfasser: Radosevich, Alexander T, Musich, Christine, Toste, F. Dean
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A vanadium-catalyzed method for the oxidative kinetic resolution of α-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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0433424