title: Enantioselective Rh(I)-Catalyzed Addition of Arylboronic Acids to Cyclic Ketimines.
abstract: A method for the enantioselective synthesis of chiral α-tertiary amines via Rh-catalyzed 1,2-addition of arylboronic acids to cyclic ketimines is described. The products are efficiently accessed in good yields and excellent enantioselectivities using a commercially available chiral ligand. The reaction scope includes vinyl, aryl, and heteroarylboronic acids with yields ranging from 40% to 99% and enantiomeric excesses from 88% to 99%. Conversion of an addition product into an α,α-diaryl-substituted amino acid is also demonstrated.
authors.affiliation: Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Jongrock
authors.initials: J
authors.lastname: Kong
authors.affiliation: Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Mark
authors.initials: M
authors.lastname: McLaughlin
authors.affiliation: Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Kevin
authors.initials: K
authors.lastname: Belyk
authors.affiliation: Process Chemistry, Merck Research Laboratories , P.O. Box 2000, Rahway, New Jersey 07065, United States.
authors.forename: Ryan
authors.initials: R
authors.lastname: Mondschein
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001897:Boronic Acids; D007097:Imines; D009570:Nitriles; C542835:ketimine; D012238:Rhodium