title: Highly stereoselective C-allylation of an enantiopure alpha-sulfinyl thioacetamide.
abstract: The alkylation of the lithium enolate of enantiopure alpha-cyclohexylsulfinyl thioacetamide 1 with allyl bromides 5 possessing an electron-withdrawing group at the vinylic position does not occur at the sulfur center - as expected in the sulfur series - but at the carbon center through conjugate addition followed by bromide elimination. The modest to excellent 1,2-asymmetric induction achieved by the alkylsulfinyl group (dr up to 100:0) is explained by an electronic model.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université de Caen, 6 Boulevard du Maréchal Juin, F-14050 Caen, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Nowaczyk
authors.forename: Carole
authors.initials: C
authors.lastname: Alayrac
authors.forename: Patrick
authors.initials: P
authors.lastname: Metzner
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Averbuch-Pouchot