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

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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

aldehydes15-hydride transferoxidative enamine catalysisSaegusa oxidationtetrahydroquinolinesH BOND FUNCTIONALIZATIONN-BOC-ALDIMINESENANTIOSELECTIVE CONJUGATE ADDITIONMANNICH-TYPE REACTIONSBETA-KETO-ESTERSBINAPHTHYL-DERIVED ORGANOCATALYSTSDIPHENYLPROLINOL SILYL ETHERQUATERNARY AMMONIUM-SALTSMICHAEL ADDITIONALPHA,BETA-UNSATURATED ALDEHYDES
제목
Asymmetric Synthesis of Tetrahydroquinolines via Saegusa-type Oxidative Enamine Catalysis/1,5-Hydride Transfer/Cyclization Sequences
저자
Suh, Chang WonWoo, Saet ByeolKim, Dae Young
DOI
10.1002/ajoc.201400022
발행일
2014-04
유형
Article
저널명
Asian Journal of Organic Chemistry
3
4
페이지
399 ~ 402