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

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90
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92

초록

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.

키워드

aldehydes; 1; 5-hydride transfer; oxidative enamine catalysis; Saegusa oxidation; tetrahydroquinolines; H BOND FUNCTIONALIZATION; N-BOC-ALDIMINES; ENANTIOSELECTIVE CONJUGATE ADDITION; MANNICH-TYPE REACTIONS; BETA-KETO-ESTERS; BINAPHTHYL-DERIVED ORGANOCATALYSTS; DIPHENYLPROLINOL SILYL ETHER; QUATERNARY AMMONIUM-SALTS; MICHAEL ADDITION; ALPHA,BETA-UNSATURATED ALDEHYDES
제목
Asymmetric Synthesis of Tetrahydroquinolines via Saegusa-type Oxidative Enamine Catalysis/1,5-Hydride Transfer/Cyclization Sequences
저자
Suh, Chang Won; Woo, Saet Byeol; Kim, Dae Young
DOI
10.1002/ajoc.201400022
발행일
2014-04
유형
Article
저널명
Asian Journal of Organic Chemistry
권
3
호
4
페이지
399 ~ 402