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
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
收藏
页码:12433 / 12438
页数:6
相关论文
共 50 条
[41]   Iron-Catalyzed Highly Enantioselective Addition of Silyl Enol Ethers to α,β-Unsaturated 2-Acyl Imidazoles [J].
Wei, Jinhu ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
ORGANIC LETTERS, 2021, 23 (17) :6993-6997
[42]   Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides [J].
Zhao MengMeng ;
Li WanFang ;
Ma Xin ;
Fan WeiZheng ;
Tao XiaoMing ;
Li XiaoMing ;
Xie XiaoMin ;
Zhang ZhaoGuo .
SCIENCE CHINA-CHEMISTRY, 2013, 56 (03) :342-348
[43]   Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines [J].
Zhang, Minghui ;
Zhang, Na ;
Zhao, Qian ;
Wang, Chao ;
Steiner, Alexander ;
Xiao, Jianliang ;
Tang, Weijun .
CHINESE CHEMICAL LETTERS, 2025, 36 (04)
[44]   Highly Selective Bis(imino)pyridine Iron-Catalyzed Alkene Hydroboration [J].
Obligacion, Jennifer V. ;
Chirik, Paul J. .
ORGANIC LETTERS, 2013, 15 (11) :2680-2683
[45]   Highly Selective and Practical Iron-Catalyzed Formal Hydrogenation of Epoxides to Primary Alcohols Using Formic Acid [J].
Yao, Yi-Xuan ;
Zhang, Hong-Wei ;
Lu, Chang-Bo ;
Shang, Hong-Yan ;
Tian, Yuan-Yu .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (14)
[46]   Iron-Catalyzed Alkylation of Alkenes and Alkynes Using Alcohols as the Alkylating Reagent [J].
Shang, Xiaojie ;
Liu, Zhong-Quan .
SYNTHESIS-STUTTGART, 2015, 47 (12) :1706-1708
[47]   Iron-Catalyzed Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes [J].
Chen, Jianhui ;
Cheng, Biao ;
Cao, Minyi ;
Lu, Zhan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (15) :4661-4664
[48]   Iron-Catalyzed Magnesium-Mediated Formal Hydroformylation of Alkynes and Alkenes [J].
Tewari, Tanuja ;
Kumar, Rohit ;
Chikkali, Samir H. .
CHEMCATCHEM, 2023, 15 (03)
[49]   Iron-Catalyzed Highly Enantioselectivecis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2 [J].
Wei, Jinhu ;
Wu, Liangliang ;
Wang, Hai-Xu ;
Zhang, Xiting ;
Tse, Chun-Wai ;
Zhou, Cong-Ying ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (38) :16561-16571
[50]   High-Activity Iron Catalysts for the Hydrogenation of Hindered, Unfunctionalized Alkenes [J].
Yu, Renyuan Pony ;
Darmon, Jonathan M. ;
Hoyt, Jordan M. ;
Margulieux, Grant W. ;
Turner, Zoe R. ;
Chirik, Paul J. .
ACS CATALYSIS, 2012, 2 (08) :1760-1764