Beta-Keto Sulfoxide reduction-stereodivergent
Click on each of the products to view the reaction mechanism with and without ZnCl2.
In the presence of ZnCl2, the hydride transfer is intermolecular yielding the R,R enantiomer. In the absence of the ZnCl2, the hydride transfer is intramolecular delivering the hydride directly yielding the R,S enantiomer.
A.Solladie-Cavallo, J. Suffert, A. Adib, G. Solladie. Tetrahedron Letters, Vol. 31, pp 6649-6652, 1990.