Highly stereoselective synthesis and application of P-chiral ferrocenyl bisphosphorus ligands for asymmetric hydrogenation

被引：24

作者：

Chen, Caiyou ^{[1
]}

Wen, Songwei ^{[1
]}

Dong, Xiu-Qin ^{[1
]}

Zhang, Xumu ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[2] South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 10期

基金：

中国国家自然科学基金;

关键词：

SUBSTITUTED CINNAMIC-ACIDS; ENANTIOSELECTIVE HYDROGENATION; NONCOVALENT INTERACTIONS; DIPHOSPHINE LIGANDS; CATALYSIS; THIOUREA;

D O I：

10.1039/c7qo00448f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New, efficient and highly stereoselective methods were developed for the synthesis/modification of Wudaphos type ligands. It was found that the "three hindered quadrant" model is crucial to ensure high enantiomeric control and that the substituents on the phosphine atom should be electron rich to increase the reactivity. Moreover, a new SPO-Wudaphos ligand was developed, which exhibited good to excellent enantioselectivities in the asymmetric hydrogenation of alpha-methylene-gamma-keto carboxylic acids.

引用

页码：2034 / 2038

页数：5

共 24 条

[1]

[Anonymous], 2010, CATALYTIC ASYMMETRIC

[2]

Blaser H U., 2010, Asymmetric Catalysis on Industrial Scale : Challenges , Approaches , and Solutions , 2nd ed

[3] Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation [J].

Chen, Caiyou ;

Zhang, Zhefan ;

Jin, Shicheng ;

Fan, Xiangru ;

Geng, Mingyu ;

Zhou, Yan ;

Wen, Songwei ;

Wang, Xinrui ;

Chung, Lung Wa ;

Dong, Xiu-Qin ;

Zhang, Xumu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) :6808-6812

[4] Ferrocenyl chiral bisphosphorus ligands for highly enantioselective asymmetric hydrogenation via noncovalent ion pair interaction [J].

Chen, Caiyou ;

Wang, Heng ;

Zhang, Zhefan ;

Jin, Shicheng ;

Wen, Songwei ;

Ji, Jianjian ;

Chung, Lung Wa ;

Dong, Xiu-Qin ;

Zhang, Xumu .

CHEMICAL SCIENCE, 2016, 7 (11) :6669-6673

[5] Stereoselective synthesis of ferrocene-based C2-symmetric diphosphine ligands:: Application to the highly enantioselective hydrogenation of α-substituted cinnamic acids [J].

Chen, Weiping ;

McCormack, Peter J. ;

Mohammed, Karim ;

Mbafor, William ;

Roberts, Stanley M. ;

Whittall, John .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4141-4144

[6] ChenPhos: Highly Modular P-Stereogenic C1-Symmetric Diphosphine Ligands for the Efficient Asymmetric Hydrogenation of α-Substituted Cinnamic Acids [J].

Chen, Weiping ;

Spindler, Felix ;

Pugin, Benoit ;

Nettekoven, Ulrike .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) :8652-8656

[7] Lewis Acids and Lewis Acid-Functionalized Ligands in Rhodium-Catalyzed Methyl Acetate Carbonylation [J].

Conifer, Christopher M. ;

Law, David J. ;

Sunley, Glenn J. ;

White, Andrew J. P. ;

Britovsek, George J. P. .

ORGANOMETALLICS, 2011, 30 (15) :4060-4066

[8]

Corey E. J., 2010, Enantioselective Chemical Synthesis: Methods, Logic and Practice

[9] Metalorganocatalysis: cooperating transition-metal catalysis and organocatalysis through a covalent bond [J].

Dong, Xiu-Qin ;

Zhao, Qingyang ;

Li, Pan ;

Chen, Caiyou ;

Zhang, Xumu .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1425-1431

[10] ASYMMETRIC HYDROGENATION OF TRISUBSTITUTED ACRYLIC ACIDS CATALYZED BY A CHIRAL (AMINOALKYL)FERROCENYLPHOSPHINE RHODIUM COMPLEX [J].

HAYASHI, T ;

KAWAMURA, N ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7876-7878

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