Tandem sequence of ArSCl initiated AdE reactions resulting in formation of two C–C bonds

Abstract

A one-pot procedure for the sequence of reactions between arylsulfanyl chloride, vinyl ether-I, vinyl ether-II and organomagnesium reagents has been developed for assembling polyfunctional compounds from simple precursors. 2,3-Dihydropyran and various vinyl ethers have been used as VE-I and/or VE-II. The dependence of the stereochemical course of the carbon–carbon bond formation step upon the Lewis acid has been studied. In the case of the sequence p-toiylsulfanyl chloride, 2,3-dihydropyran, 1-methoxy-2-methylpropene and Grignard reagent the reaction initiated with TiCl₄ takes place with a very high diastereoselectivity ( > 95%).