Asymmetric induction in the additions of anions of allylic sulfoxides to benzaldehyde

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Abstract
Addition reactions of anions of aryl allyl sulfoxides to benzaldehyde proceed readily in moderate yields and afford mixtures of products resulting from α- and γ-attack on the allyl anion. The γ-products all possess the (E)-configuration around the double bond, and asymmetric induction occurs in the addition to the extent that the major/minor diastereomer ratio exceeds 2 : 1, generally. Electronic factors are believed to be responsible for this 'remote' asymmetric induction. Mixtures of all four possible diastereomers are observed in the products from α-attack and evidence is presented which suggests that the ratios of these products are as a result of epimerization of two of the chiral centres by [2,3] sigmatropic rearrangement.

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