Thioglycolic acid (1) has been shown to undergo asymmetric addition to (2-nitroetheny1) benzene (2) in the presence of a cinchona alkaloid as a catalyst. By selection of reaction conditions, enantiomeric yields of up to 58% were obtained. Evidence is presented which supports the idea that the interaction between the carboxyl group of 1 and the active site of the catalyst (quinuclidine nitrogen) exerts a favorable effect on the extent of asymmetric ...
