IBX-Mediated Oxidation and Internal Redox Reaction Cascade: Asymmetric One-Pot Synthesis of Ring-fused Tetrahydroquinolines

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초록

Organocatalytic asymmetric synthesis of tetrahydroquinolines has been achieved via oxidation and 1,5-hydride transfer/ring-closure cascade. The feature of this research is one-pot transformation of 3-arylprop-2-en-1-ol derivatives into tetrahydroquinolines using o-iodoxybenzoic acid-mediated oxidation and internal redox reactions. The synthetically useful ring-fused tetrahydroquinoline derivatives were obtained in moderate yields and high enantioselectivity.

키워드

Asymmetric catalysis; Internal redox reaction; 1,5-Hydride transfer; Tetrahydroquinolines; ENANTIOSELECTIVE MICHAEL ADDITION; N-BOC-ALDIMINES; CHIRAL PALLADIUM COMPLEXES; MANNICH-TYPE REACTIONS; BINAPHTHYL-DERIVED ORGANOCATALYSTS; C(SP(3))-H BOND FUNCTIONALIZATION; FRIEDEL-CRAFTS ALKYLATION; QUATERNARY AMMONIUM-SALTS; MODIFIED PRIMARY AMINE; DELTA-KETO ESTERS
제목
IBX-Mediated Oxidation and Internal Redox Reaction Cascade: Asymmetric One-Pot Synthesis of Ring-fused Tetrahydroquinolines
저자
Kim, Mi Hyun; Jeong, Hyun Jung; Kim, Dae Young
DOI
10.1002/bkcs.10215
발행일
2015-04
유형
Article
저널명
Bulletin of the Korean Chemical Society
권
36
호
4
페이지
1155 ~ 1160