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

被引：84

作者：

Kang, Young Ku ^{[1
]}

Kim, Dae Young ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Asan 336745, Chungnam, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 16期

基金：

新加坡国家研究基金会;

关键词：

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; ALPHA-CYCLIZATION; TERTIARY-AMINES; BETA-KETOACIDS;

D O I：

10.1002/adsc.201300398

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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).

引用

页码：3131 / 3136

页数：6

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