COUPLING OF GRIGNARD-REAGENTS WITH ARSCL ADDUCTS OF VINYL ETHERS AS A USEFUL OPTION FOR FORMATION OF CARBON-CARBON BONDS

Adducts formed upon Ad(E) reaction of ArSCl with vinyl ethers were shown to be capable of reacting with Grignard reagents to give the corresponding beta-arylthioalkylated products. In some cases it is preferable to run the reaction in the presence Li2CuCl4. A tandem sequence of (i) ArSCl addition to tri-O-benzyl-D-glucal followed by (ii) the coupling of the resulting adduct with a set of various Grignard reagents was elaborated as a fairly general and stereoselective pathway for the preparation of 2-arylthio-2-deoxy-beta-C-glucosides.