Stereoselective Synthesis of (E)- and (Z)-γ,δ-Unsaturated Ketones Using trans-2-Phenylthiocyclobutyl Ketones

Article abstract of DOI:10.1246/cl.1993.1321

The reaction of 1-methoxymethyl-2-phenylthiocyclobutanes with phenylthiotrimethylsilane followed by hydrolysis gave (E)- and (Z)-γ,δ-unsaturated ketones with high stereoselectivity.The starting materials were easily prepared by the stereoselective addition of Grignard reagents to trans-2-phenylthiocyclobutyl ketones.