Highly stereoselective vinylogous Pummerer reaction mediated by Me3SiX

…, J Alemán, MT Aranda, MJ Arévalo, A Padwa

Index: Garcia Ruano, Jose L.; Aleman, Jose; Aranda, M. Teresa; Arevalo, Maria J.; Padwa, Albert Organic Letters, 2005 , vol. 7, # 1 p. 19 - 22

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Citation Number: 31

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%).