Stereoselective alkylation of (S)-N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones catalyzed by (Me3P)2NiCl2

Abstract

The structurally simple (Me3P)2NiCl2 complex catalyzes SN1-type alkylations of chiral N-acyl thiazolidinethiones with diarylmethyl methyl ethers and other stable carbenium cations. The former can contain a variety of functional groups and heteroatoms at the α-position. The resultant adducts are isolated as single diastereomers in high yields and can be converted into enantiomerically pure derivatives in a straightforward manner.