Regio- and stereo-selectivity in the reactions of anions of aryl allyl sulfides with benzaldehyde

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Abstract
Addition reactions of anions of aryl allyl sulfides to benzaldehyde proceed readily and in good yields and afford mixtures of products resulting from α- and γ-attack on the allyl anion. γ-Products pre- dominate, and the ratio of (E) : (Z) isomers usually surrounds unity, although in the case of the reaction involving 3-(phenylthio)but-1-ene the ratio is 10 : 1. The ratio of diastereoisomers formed in products resulting from α-attack ranges from 3 : 1 to 1.3 : 1 (starting from 3- (2,4,6-trimethyl-phenylthio)prop-1-ene and 2-methyl-3-(phenylthio)prop- 1-ene respectively).

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