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

Kyung Hee Kim, Chun Young Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6367-6374
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number12
DOIs
Publication statusPublished - 2015 Jun 19

ASJC Scopus subject areas

  • Organic Chemistry

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