title: Unusual reversal of enantioselectivity in the proline-mediated alpha-amination of aldehydes induced by tertiary amine additives.
abstract: An intriguing reversal in product enantioselectivity accompanied by a change in the kinetic profile is observed in the alpha-amination of aldehydes catalyzed by proline in the presence of organic bases. Implications for the prevailing stereochemical models for proline and related aminocatalytic transformations are discussed.
authors.affiliation: Department of Chemistry, Imperial College London SW7 2AZ, UK. blackmond@scripps.edu
authors.forename: Donna G
authors.initials: DG
authors.lastname: Blackmond
authors.forename: Antonio
authors.initials: A
authors.lastname: Moran
authors.forename: Matthew
authors.initials: M
authors.lastname: Hughes
authors.forename: Alan
authors.initials: A
authors.lastname: Armstrong
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D011392:Proline