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Asymmetric Synthesis of Tetrahydroquinolines via Saegusa‐type Oxidative Enamine Catalysis/1,5‐Hydride Transfer/Cyclization Sequences
Author(s) -
Suh Chang Won,
Woo Saet Byeol,
Kim Dae Young
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400022
Subject(s) - chemistry , enamine , enantioselective synthesis , hydride , catalysis , organocatalysis , combinatorial chemistry , redox , oxidative phosphorylation , aryl , organic chemistry , biochemistry , alkyl , hydrogen
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.