Convenient divergent strategy for the synthesis of TunePhos-type chiral diphosphine ligands and their applications in highly enantioselective Ru-catalyzed hydrogenations

被引：69

作者：

Sun, Xianfeng ^{[1
]}

Zhou, Le ^{[2
]}

Li, Wei ^{[1
]}

Zhang, Xumu ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol & Pharmaceut Chem, Piscataway, NJ 08854 USA

[2] NW A&F Univ, Coll Sci, Yangling 712100, Shaanxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 03期

关键词：

D O I：

10.1021/jo702068w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A convenient, divergent strategy for the synthesis of a series of modular and fine-tunable C-3-TunePhos-type chiral diphosphine ligands and their applications in highly efficient Ru-catalyzed asymmetric hydrogenations were explored. Up to 97 and 99% ee values were achieved for the enantio selective synthesis of beta-methyl chiral amines and alpha-hydroxy acid derivatives, respectively.

引用

页码：1143 / 1146

页数：4

共 50 条

[1] Convenient divergent strategy for the synthesis of C3*-TunePhos ligands and their applications in highly enantioselective Ru-catalyzed hydrogenations
Li, Wei
Sun, Xianfeng
Zhang, Xumu
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[2] Chiral biphosphine ligands for the Ru-catalyzed enantioselective hydrogenation of β-ketoesters
Sun, YH
Wan, XB
Guo, MJ
Wang, DH
Dong, XC
Pan, Y
Zhang, ZG
TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2185 - 2188
[3] Axially 4,4′-di-tert-butyl TunePhos-type chiral diphosphine ligand: synthesis and applications in asymmetric hydrogenation
Wang, Chun-Jiang
Wang, Chu-Bei
Chen, Dong
Yang, Guangfu
Wu, Zhengshun
Zhang, Xumu
TETRAHEDRON LETTERS, 2009, 50 (09) : 1038 - 1040
[4] Chiral diphosphine ligands based on camphor: synthesis and applications in asymmetric hydrogenations
Kadyrov, R
Ilaldinov, IZ
Almena, J
Monsees, A
Riermeier, TH
TETRAHEDRON LETTERS, 2005, 46 (43) : 7397 - 7400
[5] Highly effective chiral dipyridylphosphine ligands: Synthesis, structural determination, and applications in the Ru-catalyzed asymmetric hydrogenation reactions
Pai, CC
Lin, CW
Lin, CC
Chen, CC
Chan, ASC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11513 - 11514
[6] Axially chiral electron-rich TunePhos-type ligand: synthesis and applications in asymmetric hydrogenation
Zou, Yaping
Geng, Huiling
Zhang, Weicheng
Yu, Shichao
Zhang, Xumu
TETRAHEDRON LETTERS, 2009, 50 (42) : 5777 - 5779
[7] Synthesis of Stable Phosphomide Ligands and their Use in Ru-Catalyzed Hydrogenations of Bicarbonate and Related Substrates
Gowrisankar, Saravanan
Federsel, Christopher
Neumann, Helfried
Ziebart, Carolin
Jackstell, Ralf
Spannenberg, Anke
Beller, Matthias
CHEMSUSCHEM, 2013, 6 (01) : 85 - 91
[8] A New Class of Tunable Dendritic Diphosphine Ligands: Synthesis and Applications in the Ru-Catalyzed Asymmetric Hydrogenation of Functionalized Ketones
Ma, Baode
Miao, Tingting
Sun, Yihua
He, Yanmei
Liu, Ji
Feng, Yu
Chen, Hui
Fan, Qing-Hua
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (32) : 9969 - 9978
[9] Axial Chirality Control by 2,4-Pentanediol for the Alternative Synthesis of C3*-TunePhos Chiral Diphosphine Ligands and Their Applications in Highly Enantioselective Ruthenium-Catalyzed Hydrogenation of β-Keto Esters
Sun, Xianfeng
Li, Wei
Hou, Guohua
Zhou, Le
Zhang, Xumu
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) : 2553 - 2557
[10] Straightforward Synthesis of Chiral Terpenoid Building Blocks by Ru-Catalyzed Enantioselective Hydrogenation
Ruiz, Johal
Oger, Philippe
Soulere, Laurent
Popowycz, Florence
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9396 - 9406

← 1 2 3 4 5 →