title: Acetoxyl group directed cyclization promoted by SmI2: directing group determined stereocomplementarity.
abstract: Complete reversal of diastereoselectivity was observed in the SmI(2)-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI(2)-induced ketyl-olefin coupling cyclizations of the delta-hydroxy ketone 1 and delta-acetoxy ketone 3.
authors.affiliation: Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
authors.forename: Seijiro
authors.initials: S
authors.lastname: Hosokawa
authors.forename: Shinji
authors.initials: S
authors.lastname: Nara
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Tamiya
authors.forename: Haruhisa
authors.initials: H
authors.lastname: Shirahama
authors.forename: Fuyuhiko
authors.initials: F
authors.lastname: Matsuda