Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones

Do Young Park, Kyung Hee Kim, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A new protocol for the synthesis of chiral β-aminotetralins has been developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of β-tetralones using a Hantzsch ester as an organic hydride donor. Various chiral β-aminotetralins were obtained in good yields with good to high enantioselectivities. Furthermore, the utility of our new protocol was successfully demonstrated in the enantioselective synthesis of rotigotine. (Figure presented.).

Original languageEnglish
Pages (from-to)462-467
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number3
DOIs
Publication statusPublished - 2018 Feb 1

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-20100020209 and NRF-2015R1D1 A1 A01057200). C.-H.C. also thanks for a financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis). We also thank Professor Jianwei Sun for providing us with SP-CPA.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Asymmetric reductive amination
  • Chiral phosphoric acid catalysis
  • Rotigotine
  • β-Aminotetralins
  • β-Tetralones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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