title: Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration.
abstract: Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper-catalyzed 1,6-boration of electron-deficient dienes with bis(pinacolato)diboron (B2(pin)2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol %. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using only a 0.02 mol % catalyst loading.
authors.affiliation: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK); School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK) http://www.nottingham.ac.uk/∼pczhl.
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Luo
authors.forename: Iain D
authors.initials: ID
authors.lastname: Roy
authors.forename: Amaël G E
authors.initials: AG
authors.lastname: Madec
authors.forename: Hon Wai
authors.initials: HW
authors.lastname: Lam
mesh_terms: D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D020005:Propanols; C006463:allyl alcohol; D003300:Copper; D001895:Boron
keywords: 1,6-addition; asymmetric catalysis; boron; copper; enantioselectivity