Organic Synthesis Utilizing 2-Phenylthiocyclobutyl Ketones1

Abstract

The organic synthesis utilizing 2-phenylthiocyclobutyl ketones, prepared by the [2+2] cycloaddition of 1-alkenyl sulfides with vinyl ketones, as starting materials are described. The preparations of 1-acetyl-1,3,5-cyclooctatrienes, hydrindanones, 4-acetylcyclohexenes, (Z)-enol trimethylsilyl ethers, and 1,1,5-trisubstituted (E)- and (Z)-1,5-dienes were achieved utilizing 1-cyclobutenyl ketones, prepared from 2-phenylthiocyclobutyl ketones by the oxidation and β-elimination of phenylthio group. The addition of organometallics to 2-phenylthiocyclobutyl ketones and following ring opening reactions also gave (E)- and (Z)-trisubstituted olefins having various functional groups with high stereoselectivity.