Metal-Catalyzed Oxidation and Epoxidation of α-Hydroxy Vinyl and Dienyl Sulfoxides

Treatment of acyclic α-hydroxyalkyl α,β-unsaturated sulfoxides with t-BuOOH/VO(acac)2 results in rapid oxidation to the unsaturated sulfones followed by an unusual regio- and stereoselective epoxidation at the unsaturated sulfones; this methodology has been applied to the preparation of carbohydrate...

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Veröffentlicht in:Journal of organic chemistry 2006-02, Vol.71 (4), p.1569-1575
Hauptverfasser: Fernández de la Pradilla, Roberto, Castellanos, Alejandro, Fernández, Jorge, Lorenzo, Milagros, Manzano, Pilar, Méndez, Paloma, Priego, Julián, Viso, Alma
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Sprache:eng
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Zusammenfassung:Treatment of acyclic α-hydroxyalkyl α,β-unsaturated sulfoxides with t-BuOOH/VO(acac)2 results in rapid oxidation to the unsaturated sulfones followed by an unusual regio- and stereoselective epoxidation at the unsaturated sulfones; this methodology has been applied to the preparation of carbohydrate-like fragments.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052244d