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 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo052244d |