Rh-catalyzed asymmetric hydrogenation of α-aryl imino esters:: An efficient enantioselective synthesis of aryl glycine derivatives

被引：115

作者：

Shang, Gao ^{[1
]}

Yang, Qin ^{[1
]}

Zhang, Xumu ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 38期

关键词：

amino acids; asymmetric catalysis; enantioselectivity; hydrogenation; reduction;

D O I：

10.1002/anie.200601540

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A highly enantioselective synthesis of aryl glycine derivatives from asymmetric hydrogenation was achieved by subjecting N-PMP-protected α-aryl imino esters to hydrogenation under Rh-bisphosphine catalysis (see scheme; PMP = para-methoxyphenyl, cod = cycloocta-1,5-diene). The PMP group could be easily removed for the preparation of enantiomerically pure aryl glycine derivatives. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6360 / 6362

页数：3

共 50 条

[1] Enantioselective Synthesis of Optically Pure β-Amino Ketones and γ-Aryl Amines by Rh-Catalyzed Asymmetric Hydrogenation
Geng, Huiling
Huang, Kexuan
Sun, Tian
Li, Wei
Zhang, Xiaowei
Zhou, Le
Wu, Wenjun
Zhang, Xumu
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01): : 332 - 334
[2] Rh-catalyzed asymmetric hydrogenation of γ-phthalimido-substituted α,β-unsaturated carboxylic acid esters:: An efficient enantioselective synthesis of β-aryl-γ-amino acids
Deng, Jun
Duan, Zheng-Chao
Huang, Jia-Di
Hu, Xiang-Ping
Wang, Dao-Yong
Yu, Sai-Bo
Xu, Xue-Feng
Zheng, Zhuo
ORGANIC LETTERS, 2007, 9 (23) : 4825 - 4828
[3] Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines
Liu, Dan
Li, Bowen
Chen, Jianzhong
Gridnev, Ilya D.
Yan, Deyue
Zhang, Wanbin
NATURE COMMUNICATIONS, 2020, 11 (01)
[4] Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines
Dan Liu
Bowen Li
Jianzhong Chen
Ilya D. Gridnev
Deyue Yan
Wanbin Zhang
Nature Communications, 11
[5] Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation
Yan, Qiaozhi
Xiao, Guiying
Wang, Ying
Zi, Guofu
Zhang, Zhanbin
Hou, Guohua
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (04) : 1749 - 1756
[6] Asymmetric synthesis of chiral glutaric acid derivatives via Rh-catalyzed enantioselective hydrogenation
Duan, Zheng-Chao
Hu, Xiang-Ping
Deng, Jun
Yu, Sai-Bo
Wang, Dao-Yong
Zheng, Zhuo
TETRAHEDRON-ASYMMETRY, 2009, 20 (05) : 588 - 592
[7] Rh-catalyzed asymmetric hydrogenation of α-aryl-β-alkylvinyl esters with chiral ferrocenylphosphine-phosphoramidite ligand
Dong, Chao
Liu, Dao-Sheng
Zhang, Lei
Hu, Xiang-Ping
TETRAHEDRON LETTERS, 2021, 65
[8] Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation
Lang, Qiwei
Gu, Guoxian
Cheng, Yaoti
Yin, Qin
Zhang, Xumu
ACS CATALYSIS, 2018, 8 (06): : 4824 - 4828
[9] Rh-catalyzed asymmetric hydrogenation of γ-phthalimido-substituted α,β-unsaturated carboxylic acid esters:: An efficient enantioselective synthesis of β-aryl-γ-amino acids (vol 9, pg 4827, 2007)
Deng, Jun
Duan, Zheng-Chao
Huang, Jia-Di
Hu, Xiang-Ping
Wang, Dao-Yong
Yu, Sal-Bo
Xu, Xue-Feng
Zheng, Zhuo
ORGANIC LETTERS, 2008, 10 (15) : 3379 - 3379
[10] Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters
Yan, Qiaozhi
Shen, Xin
Zi, Guofu
Hou, Guohua
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (27) : 5961 - 5964

← 1 2 3 4 5 →