title: Enantioselective Carbon-Carbon Bond Formation via S(N)2' Displacements of Acyclic Allylic Mesylates(1).
abstract: The copper-mediated S(N)2' displacement of enantiomerically pure allylic mesyloxy vinyl sulfoxides takes place with high yields and stereoselectivities. In these adducts, the newly created chiral center is adjacent to a vinyl sulfoxide functionality which should allow for subsequent chirality transfer operations. Alternatively, enantiopure alkenyl sulfones and alkenes bearing an allylic stereocenter are readily available from these adducts with high geometric control. The S(N)2' displacements of structurally related mesyloxy sulfides and sulfones with organocuprates have been examined. From a single enantiomer at the allylic alcohol position, the absolute configuration of the new chiral center may be controlled by adjusting the oxidation level on sulfur.
authors.affiliation: Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain.
authors.forename: Joseph P.
authors.initials: JP
authors.lastname: Marino
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
authors.forename: Jae-Don
authors.initials: JD
authors.lastname: Lee
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández De La Pradilla
authors.forename: Paloma
authors.initials: P
authors.lastname: Fernández
authors.forename: M. Belén
authors.initials: MB
authors.lastname: Rubio