Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

DJ Antonjuk, DD Ridley and MA Smal

Australian Journal of Chemistry 33(12) 2635 - 2651
Published: 1980

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.

https://doi.org/10.1071/CH9802635

© CSIRO 1980

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions

View Altmetrics