title: Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.
abstract: Catalytic allylboron additions to aldimines are presented for which small amounts of Zn(OMe)2 serve as the co-catalyst to accelerate allyl exchange and 1,3-borotropic shift processes. Low-yielding and moderately α- and diastereoselective reactions are thus turned into highly efficient γ-, diastereo-, and enantioselective transformations that exhibit considerable scope.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Farid W
authors.initials: FW
authors.lastname: van der Mei
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Miyamoto
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Silverio
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA. amir.hoveyda@bc.edu.
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D058116:Lewis Acids; D001895:Boron
keywords: boron; borotropic shift; diastereoselective  synthesis; enantioselective  catalysis; homoallylic amines