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

Do Young Park; Kyung Hee Kim; Cheol-Hong Cheon

doi:10.1002/adsc.201701198

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

Do Young Park, Kyung Hee Kim, Cheol-Hong Cheon

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Journal	Advanced Synthesis and Catalysis
DOIs	https://doi.org/10.1002/adsc.201701198
Publication status	Accepted/In press - 2017 Jan 1

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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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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AU - Kim, Kyung Hee

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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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KW - β-Aminotetralins

KW - β-Tetralones

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