α-METHOXYALLYL SULFIDES AS A NOVEL HOMOENOLATE DIANION EQUIVALENT

Article abstract of DOI:10.1016/S0040-4039(01)81719-6

α-Methoxyallyl sulfides 1 proved to serve a novel homoenolate dianion equivalent.Introduction of two electrophiles into 1 was realized by successive regiospecific reaction of an allylic moiety with electrophiles intervented by an acid-catalyzed thioallylic rearrangement.Facile desulfurization of the products under mild conditions afforded a variety of α,β-unsaturated carbonyl compounds and 2,3,4-trisubstituted furans.