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Stereospecific Nucleophilic Addition Reactions to Olefins. Addition of Thiols to alpha,beta-Unsaturated Carboxylic Acid Derivatives

Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-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.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H823NO – PubChem