title: A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.
abstract: Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral (10)B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.
authors.forename: Chunrui
authors.initials: C
authors.lastname: Sun
authors.forename: Bowman
authors.initials: B
authors.lastname: Potter
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; D001895:Boron