Asymmetric Synthesis of Tetrahydroquinolines via 1,5-Hydride Transfer/Cyclization Catalyzed by Chiral Primary Amine Catalysts

Citations

WEB OF SCIENCE

88
Citations

SCOPUS

93

초록

Chiral primary amine-catalyzed asymmetric CH functionalization has been achieved. In this process, enantiotopic Csp(3)H functionalization at the -position to the nitrogen atom of 4-[ortho-(dialkylamino)phenyl]but-3-en-2-one is activated by chiral 9-amino(9-deoxy)-epi-quinine to afford tetrahydroquinine derivatives with high enantioselectivities (up to 97% ee).

키워드

asymmetric synthesis; CH functionalization; 1; 5-hydride transfer; organocatalysis; tetrahydroquinolines; H BOND FUNCTIONALIZATION; RING-CLOSURE REACTIONS; HYDRIDE TRANSFER; C-C; TRANSFER HYDROGENATION; STEREOCHEMICAL ASPECTS; HETEROCYCLIC SYNTHESIS; CARBONYL-COMPOUNDS; ALPHA-CYCLIZATION; TERTIARY-AMINES
제목
Asymmetric Synthesis of Tetrahydroquinolines via 1,5-Hydride Transfer/Cyclization Catalyzed by Chiral Primary Amine Catalysts
저자
Kang, Young Ku; Kim, Dae Young
DOI
10.1002/adsc.201300398
발행일
2013-11-11
유형
Article
저널명
Journal für Praktische Chemie
권
355
호
16
페이지
3131 ~ 3136