Stereospecific Nucleophilic Addition Reactions to Olefins. Addition of Thiols to α,β-Unsaturated Carboxylic Acid Derivatives

Article abstract of DOI:10.1021/jo00023a021

Stereospecific nucleophilic addition of thiols to derivatives of α,β-unsaturated carboxylic acids is described.The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source.Erythro and threo adducts are obtained with high diastereoselectivity from E and Z olefins, respectively.This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.