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

8 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 language	English
Pages (from-to)	462-467
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	3
DOIs	https://doi.org/10.1002/adsc.201701198
Publication status	Published - 2018 Feb 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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10.1002/adsc.201701198

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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. (Figure presented.).",

keywords = "Asymmetric reductive amination, Chiral phosphoric acid catalysis, Rotigotine, β-Aminotetralins, β-Tetralones",

author = "Park, {Do Young} and Kim, {Kyung Hee} and Cheon, {Cheol Hong}",

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: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

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doi = "10.1002/adsc.201701198",

language = "English",

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AU - Park, Do Young

AU - Kim, Kyung Hee

AU - Cheon, Cheol Hong

N1 - 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

PY - 2018/2/1

Y1 - 2018/2/1

N2 - 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.).

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. (Figure presented.).

KW - Asymmetric reductive amination

KW - Chiral phosphoric acid catalysis

KW - Rotigotine

KW - β-Aminotetralins

KW - β-Tetralones

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DO - 10.1002/adsc.201701198

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SN - 1615-4150

VL - 360

SP - 462

EP - 467

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 3

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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