Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination

Kim, K.-H.; Lee, C.-Y.; Cheon, C.-H.

Journal of Organic Chemistry 80(12): 6367-6374


ISSN/ISBN: 1520-6904
PMID: 26000470
DOI: 10.1021/acs.joc.5b00812
Accession: 057760187

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A new method for the synthesis of chiral β-aryl amines via chiral phosphoric acid-catalyzed enantioselective reductive amination of benzyl methyl ketone derivatives with Hantzsch ester was developed. Various chiral β-aryl amines were obtained in high yields and with good to high enantioselectivities. This transformation is applicable to gram-scale reactions, and the catalyst loading can be reduced to 1 mol % without sacrificing any catalytic efficacy. Furthermore, the resulting β-aryl amine was successfully converted into a tetrahydroisoquinoline compound without any loss of enantioselectivity.