Electrophilic Olefin Heterocyclization in Organic Synthesis. Stereoselective Synthesis of 4,5-Disubstituted γ-Lactams by Iodine-Induced Lactam Formation of γ,δ-Unsaturated Thioimidates

Article abstract of DOI:10.1021/jo00281a022

Iodine-induced lactamization of γ,δ-unsaturated thioimidates proceeds regioselectively to provide γ-lactams.The iodolactamization with allylic substituents brings about 1,2-asymmetric induction, which depends on the allyl groups.Transformation of the cis-4-hydroxy-5-(iodomethyl)pyrrolidin-2-one (24a) among these highly functionalized γ-lactams into several biologically active compounds is described.In addition, the conversion of an optically active form of 24a is discussed.