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 journalArticle

3 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.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2017 Jan 1

Fingerprint

Tetralones
Amination
Phosphoric acid
Enantioselectivity
Hydrides
Esters
phosphoric acid

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones",
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.",
keywords = "Asymmetric reductive amination, Chiral phosphoric acid catalysis, Rotigotine, β-Aminotetralins, β-Tetralones",
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language = "English",
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AU - Kim, Kyung Hee

AU - Cheon, Cheol-Hong

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AB - 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.

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