
TY  - JOUR
A1  - Antonjuk, DJ 
A1  - Ridley, DD 
A1  - Smal, MA 
T1  - Asymmetric induction in the additions of anions of allylic sulfoxides to benzaldehyde
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 12
SP  - 2635
EP  - 2651
KW  - 
UR  - https://doi.org/10.1071/CH9802635 
N2  - 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. 
ER  -

