title: A novel catalytic asymmetric route towards skipped dienes with a methyl-substituted central stereogenic carbon.
abstract: A highly efficient method for the enantioselective synthesis of 1,4-dienes (skipped dienes) with a methyl-substituted central stereogenic carbon using copper-catalysed asymmetric allylic alkylation of diene bromides was developed. Excellent regio- and enantioselectivity (up to 97 : 3 SN2'/SN2 ratio and 99% ee) were achieved with broad substrate scope.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Yange
authors.initials: Y
authors.lastname: Huang
authors.forename: Martín
authors.initials: M
authors.lastname: Fañanás-Mastral
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000478:Alkylation; D001965:Bromides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001965:Bromides; D002244:Carbon; D003300:Copper