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Reaction of allylic dithioacetals with organocuprate or organolithium reagent followed by treatment with a variety of alkyl electrophiles gives the corresponding E and Z isomeric mixture of vinyl sulfides in good yield. Further cross coupling with a Grignard reagent in the presence of NiCl2(dppe) affords the corresponding alkylation products in good yield. In general, the Grignard reagent having the same alkyl group as the R2 substituent in 1 is employed so that the stereochemical problem in coupling products can be lifted.

Allylic Dithioacetal as a Propene-1,3-Zwitterion Synthon. Regioselective Conversion of C-S Bonds in Allylic Dithioacetals into C-C Bonds