title: Catalytic Asymmetric Synthesis of Phosphine Boronates.
abstract: The first catalytic enantioselective synthesis of ambiphilic phosphine boronate esters is presented. The asymmetric boration of α,β-unsaturated phosphine oxides catalyzed by a copper bisphosphine complex affords optically active organoboronate esters that bear a vicinal phosphine oxide group in good yields and high enantiomeric excess. The synthetic utility of the products is demonstrated through stereospecific transformations into multifunctional optically active compounds.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands). v.hornillos.gomez.recuero@rug.nl.
authors.forename: Valentín
authors.initials: V
authors.lastname: Hornillos
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands).
authors.forename: Carlos
authors.initials: C
authors.lastname: Vila
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands).
authors.forename: Edwin
authors.initials: E
authors.lastname: Otten
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands). b.l.feringa@rug.nl.
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D004952:Esters; D010087:Oxides; D010720:Phosphines; D003300:Copper; C044646:phosphine
keywords: asymmetric catalysis; borylation; copper catalysis; organophosphorus compounds; phosphine boronates