Use of electrochemical methods as an alternative to tin reagents for the reduction of vinyl halides in inositol synthons

Several vinyl halides previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allyl ic ethers at the applied potentials allowed the selective reduction of viny l halides to olefins. Electrochemical methods provide for selective reducti on of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology. Cinnamyl ethers were reductively cleaved at -3.2 V (vs Agl AgNO(3)) in the presence of alkyl allyl ethers to provide selective deprote ction. The electrochemical reduction of vinyl halides in the presence of a vinyloxirane or vinylaziridine is accompanied by the solvolysis of the stra ined rings. Yields and conditions are reported and compared to those from s tandard tin-induced dehalogenation.