Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes

被引：41

作者：

Lu, Peng ^{[1
]}

Ren, Xiang ^{[1
]}

Xu, Haofeng ^{[1
]}

Lu, Dongpo ^{[1
]}

Sun, Yufeng ^{[1
]}

Lu, Zhan ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 32期

关键词：

ASYMMETRIC HYDROGENATION; HYDROBORATION; COMPLEXES; OLEFINS; HYDROSILYLATION; EFFICIENT; LIGANDS; ROUTE;

D O I：

10.1021/jacs.1c04773

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.

引用

页码：12433 / 12438

页数：6

共 50 条

[21] Iron-Catalyzed Hydrogenation of Amides to Alcohols and Amines [J].

Rezayee, Nomaan M. ;

Samblanet, Danielle C. ;

Sanford, Melanie S. .

ACS CATALYSIS, 2016, 6 (10) :6377-6383

[22] Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids [J].

Du, Xiaoyong ;

Xiao, Ye ;

Huang, Jia-Ming ;

Zhang, Yao ;

Duan, Ya-Nan ;

Wang, Heng ;

Shi, Chuan ;

Chen, Gen-Qiang ;

Zhang, Xumu .

NATURE COMMUNICATIONS, 2020, 11 (01)

[23] TacklingN-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines [J].

Blasius, Clemens K. ;

Heinrich, Niklas F. ;

Vasilenko, Vladislav ;

Gade, Lutz H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (37) :15974-15977

[24] Iridium-Catalyzed Highly Enantioselective Hydrogenation of Exocyclic α,β-Unsaturated Carbonyl Compounds [J].

Tian, Fengtao ;

Yao, Dongmei ;

Liu, Yuanyuan ;

Xie, Fang ;

Zhang, Wanbin .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (11-12) :1841-1845

[25] Recent progress in cobalt-catalyzed enantioselective hydrogenation and hydroboration reactions of alkenes [J].

Yang, Xiaoxu ;

Ge, Shaozhong .

CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, 2021, 31

[26] Selective iron-catalyzed transfer hydrogenation of terminal alkynes [J].

Wienhoefer, Gerrit ;

Westerhaus, Felix A. ;

Jagadeesh, Rajenahally V. ;

Junge, Kathrin ;

Junge, Henrik ;

Beller, Matthias .

CHEMICAL COMMUNICATIONS, 2012, 48 (40) :4827-4829

[27] Iridium-Catalyzed Enantioselective Hydrogenation of Cyclic Imines [J].

Chang, Mingxin ;

Li, Wei ;

Hou, Guohua ;

Zhang, Xumu .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3121-3125

[28] Ultrafast Iron-Catalyzed Reduction of Functionalized Ketones: Highly Enantioselective Synthesis of Halohydrines, Oxaheterocycles, and Aminoalcohols [J].

Blasius, Clemens K. ;

Vasilenko, Vladislav ;

Gade, Lutz H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) :10231-10235

[29] First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates [J].

Li, Shengkun ;

Xiao, Taifeng ;

Li, Dangdang ;

Zhang, Xumu .

ORGANIC LETTERS, 2015, 17 (15) :3782-3785

[30] Highly enantioselective Ir-catalyzed hydrogenation of exocyclic enamines [J].

Wang, Xiao-Bing ;

Wang, Da-Wei ;

Lu, Sheng-Mei ;

Yu, Chang-Bin ;

Zhou, Yong-Gui .

TETRAHEDRON-ASYMMETRY, 2009, 20 (09) :1040-1045

← 1 2 3 4 5 →