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
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
收藏
页码:3131 / 3136
页数:6
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