
%0 Journal Article
%A Antonjuk, DJ 
%A Ridley, DD 
%A Smal, MA 
%T Asymmetric induction in the additions of anions of allylic sulfoxides to benzaldehyde
%J Australian Journal of Chemistry
%D 1980/12/01
%V 33
%N 12
%P 2635-2651
%K 
%R https://doi.org/10.1071/CH9802635
%U https://www.publish.csiro.au/paper/CH9802635 
%X Addition reactions of anions of aryl allyl sulfoxides to benzaldehyde proceed readily in moderate yields and afford mixtures of products resulting from &#945;- and &#947;-attack on the allyl anion. The &#947;-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 &#945;-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. 
