Iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts

被引：26

作者：

Ji, Yue ^{[1
,2
]}

Feng, Guang-Shou ^{[1
]}

Chen, Mu-Wang ^{[1
]}

Shi, Lei ^{[1
,3
]}

Du, Haifeng ^{[3
]}

Zhou, Yong-Gui ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 06期

基金：

中国国家自然科学基金;

关键词：

BETA-CARBOLINE ALKALOIDS; N-H IMINES; ENANTIOSELECTIVE SYNTHESIS; HETEROAROMATIC-COMPOUNDS; PYRIDINIUM SALTS; PAENIBACILLUS-LACTIS; (R)-IMINE REDUCTASE; AQUEOUS-MEDIA; ANION-BINDING; TETRAHYDROISOQUINOLINE;

D O I：

10.1039/c7qo00060j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective hydrogenation of cyclic iminium salts has been successfully realized by employing [Ir(COD)Cl](2) and chiral diphosphine ligands as catalyst, furnishing chiral N-alkyl tetrahydroisoquinolines and N-alkyl tetrahydro-beta-carbolines with up to 96% ee and 88% ee, respectively. The hydrogenation provides a direct, simple and efficient protocol toward chiral tertiary amines. Meanwhile, asymmetric hydrogenation at the gram scale was also conducted smoothly without loss of reactivity and enantioselectivity.

引用

页码：1125 / 1129

页数：5

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