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Highly stereoselective vinylogous Pummerer reaction mediated by Me3SiX
Jose L García Ruano1, José Alemán, M Teresa Aranda
1Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
Organic Letters
|December 31, 2004
Abstract:
A highly stereoselective vinylogous Pummerer rearrangement involving 1,4-migration of the sulfinyl oxygen atom occurs when ortho-sulfinyl benzyl carbanions are treated with trimethylsilyl halides. The reaction proceeds in good yield and affords optically pure benzyl alcohols with extremely high enantioselectivity (ee > 98%).