title: Enantioselective copper-catalyzed allylic alkylation with dialkylzincs using phosphoramidite ligands.
abstract: [reaction: see text]. In the presence of a catalytic amount of copper salts, cinnamyl halides undergo a regio- and enantioselective S(N)2' alkylation with dialkylzincs using chiral phosphoramidites as ligands. An S(N)2':S(N)2 ratio of 85:15 and enantiomeric excesses up to 77% for the chiral S(N)2' products are found. Variation of solvent and reaction temperature revealed that the highest regio- and enantioselectivities are found using coordinating solvents of -40 degrees C.
authors.affiliation: Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: H
authors.initials: H
authors.lastname: Malda
authors.forename: A W
authors.initials: AW
authors.lastname: van Zijl
authors.forename: L A
authors.initials: LA
authors.lastname: Arnold
authors.forename: B L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000477:Alkylating Agents; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors; D015032:Zinc / Q000737:chemistry*
chemical_list: D000477:Alkylating Agents; D008024:Ligands; D009943:Organophosphorus Compounds; D003300:Copper; D015032:Zinc