4.5 Article

Asymmetric Synthesis of Tetrahydroquinolines via Saegusa-type Oxidative Enamine Catalysis/1,5-Hydride Transfer/Cyclization Sequences

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 3, Issue 4, Pages 399-402

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201400022

Keywords

aldehydes; 1; 5-hydride transfer; oxidative enamine catalysis; Saegusa oxidation; tetrahydroquinolines

Funding

  1. Soonchunhyang University Research Fund
  2. National Research Foundation of Korea (NRF) - Ministry of Education, Science and Technology [2013-052688]

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Enantioselective organocatalytic synthesis of tetrahydroquinolines has been achieved via Saegusa-type oxidative enamine catalysis/1,5-hydride transfer/cyclization sequences. The feature of this research is a one-pot transformation of 3-aryl aldehydes into tetrahydroquinolines by using environmentally benign catalytic Saegusa oxidation and highly efficient internal redox reactions. The synthetically useful ring-fused tetrahydroquinoline derivatives were obtained in moderate yields and high levels of enantioselectivity.

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