title: A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.
abstract: The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting α-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched α-arylamino ketones. A serendipitous kinetic resolution of racemic α-arylamino hydrazones is also described.
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States.|Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: Dillon H
authors.initials: DH
authors.lastname: Miles
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States.|Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: Joan
authors.initials: J
authors.lastname: Guasch
authors.affiliation: Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States.|Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000586:Amination; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000814:Aniline Compounds; D006835:Hydrazones; D006841:Hydrocarbons, Aromatic; D007659:Ketones