Base-catalyzed inversion of chiral sulfur centers. A computational study

A theoretical study on the pyramidal inversion of the chiral sulfur compounds SO(X)(Me) (X = Cl, OMe, p-MePh) has been carried out by means of the DFT(Becke3LYP) method. Our results reveal that in the case of X = Cl, an organic tertiary amine such as NMe(3) can catalyze the racemization. The base-catalyzed inversion of SO(Cl)(Me) is proposed as a feasible dynamic kinetic resolution mechanism for the synthesis of chiral sulfoxides by the DAG method.