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A highly stereoselective vinylogous Pu
mmerer rearrange
ment involving 1,4-
migration of the sulfinyl oxygen ato
m occurs when
ortho-sulfinylbenzyl carbanions are treated with tri
methylsilyl halides. The reaction proceeds in good yield and affords optically pure benzyl alcohols withextre
mely high enantioselectivity (ee > 98%).