Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes

被引：37

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

[41] IRON-CATALYZED ADDITION-REACTION OF FLUOROALKYL IODIDES TO ALKENES
CHEN, QY
HE, YB
YANG, ZY
JOURNAL OF FLUORINE CHEMISTRY, 1986, 34 (02) : 255 - 258
[42] Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Alkenes
Kshirsagar, Umesh A.
Regev, Clil
Parnes, Regev
Pappo, Doron
ORGANIC LETTERS, 2013, 15 (12) : 3174 - 3177
[43] Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides
Liu, Weiping
Li, Yuanming
Liu, Kaisheng
Li, Zhiping
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (28) : 10756 - 10759
[44] Iron-Catalyzed Directed Alkylation of Alkenes and Arenes with Alkylzinc Halides
Ilies, Laurean
Ichikawa, Saki
Asako, Sobi
Matsubara, Tatsuaki
Nakamura, Eiichi
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2175 - 2179
[45] Iron-catalyzed regioselective protoboration of alkenes on N-heterocycles
Zou, Chenchen
Zhang, Chun
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (22) : 6325 - 6330
[46] Iron-catalyzed direct difunctionalization of alkenes with dioxygen and sulfinic acids: a highly efficient and green approach to β-ketosulfones
Wei, Wei
Wen, Jiangwei
Yang, Daoshan
Wu, Min
You, Jinmao
Wang, Hua
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (39) : 7678 - 7681
[47] Iron-Catalyzed Cascade Carbochloromethylation of Activated Alkenes: Highly Efficient Access to Chloro-Containing Oxindoles
Lu, Ming-Zhu
Loh, Teck-Peng
ORGANIC LETTERS, 2014, 16 (18) : 4698 - 4701
[48] Iron-Catalyzed Enantioselective Si-H Bond Insertions
Gu, Haorui
Han, Zhao
Xie, Hujun
Lin, Xufeng
ORGANIC LETTERS, 2018, 20 (20) : 6544 - 6549
[49] Iron-Catalyzed Highly Enantioselective Addition of Silyl Enol Ethers to α,β-Unsaturated 2-Acyl Imidazoles
Wei, Jinhu
Huang, Jie-Sheng
Che, Chi-Ming
ORGANIC LETTERS, 2021, 23 (17) : 6993 - 6997
[50] Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions
Legros, J
Bolm, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (32) : 4225 - 4228

← 1 2 3 4 5 →