Enantioselective One-Pot Synthesis of Ring-Fused Tetrahydroquinolines via Aerobic Oxidation and 1,5-Hydride Transfer/Cyclization Sequences

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초록

Enantioselective organocatalytic synthesis of tetrahydroquinolines has been achieved via an aerobic oxidation and a 1,5-hydride transfer/cyclization sequence. The feature of this research is a one-pot transformation of 3-arylprop-2-en-1-ol derivatives into tetrahydroquinolines using a Ru(VII)-catalyzed aerobic oxidation and highly efficient internal redox reactions. The synthetically useful ring-fused tetrahydroquinoline derivatives are obtained in moderate yields and high levels of enantioselectivity.

키워드

Tetrahydroquinolines; 1; 5-Hydride transfer; aymmetric catalysis; C-H FUNCTIONALIZATION; N-BOC-ALDIMINES; MANNICH-TYPE REACTIONS; C(SP(3))-H BOND FUNCTIONALIZATION; ASYMMETRIC MICHAEL ADDITION; QUATERNARY AMMONIUM-SALTS; ALPHA-KETO ESTERS; CONJUGATE ADDITION; HYDRIDE TRANSFER; ALPHA,BETA-UNSATURATED KETONES
제목
Enantioselective One-Pot Synthesis of Ring-Fused Tetrahydroquinolines via Aerobic Oxidation and 1,5-Hydride Transfer/Cyclization Sequences
저자
Suh, Chang Won; Kim, Dae Young
DOI
10.1021/ol502575f
발행일
2014-10-17
유형
Article
저널명
Organic Letters
권
16
호
20
페이지
5374 ~ 5377