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Asymmetric Induction in the Additions of Anions of Allylic Sulfoxides to Benzaldehyde
Antonjuk, David J.,Ridley, Damon D.,Smal, Mary A.
, p. 2635 - 2651 (2007/10/02)
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 sigmatropic rearrangement.
