4.7 Article

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

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 3, Pages 462-467

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701198

Keywords

beta-Aminotetralins; Asymmetric reductive amination; Chiral phosphoric acid catalysis; Rotigotine; beta-Tetralones

Funding

  1. National Research Foundation of Korea (NRF) - Korean Government [NRF-20100020209, NRF-2015R1D1 A1 A01057200]
  2. NRF
  3. Korean Government (Center for New Directions in Organic Synthesis) [NRF-2014-011165]

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A new protocol for the synthesis of chiral beta-aminotetralins has been developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of beta-tetralones using a Hantzsch ester as an organic hydride donor. Various chiral beta-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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