Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation

被引：54

作者：

Li, Pan ^{[1
,2
]}

Huang, Yi ^{[2
]}

Hu, Xinquan ^{[1
]}

Dong, Xiu-Qin ^{[2
]}

Zhang, Xumu ^{[2
,3
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[3] South Univ Sci & Technol China, Dept Chem, Shenzhen 518000, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

中国国家自然科学基金;

关键词：

RUTHENIUM-DIAMINE CATALYSTS; ENANTIOSELECTIVE SYNTHESIS; BENZODIAZEPINES; METATHESIS; DISCOVERY; IMINES; ACID;

D O I：

10.1021/acs.orglett.7b01726

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.

引用

页码：3855 / 3858

页数：4

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