Asymmetric hydrogenation of α-arylacrylic and β-arylbut-3-enoic acids catalyzed by a Rh(I) complex of a monodentate secondary phosphine oxide ligand

被引:31
作者
Dong, Kaiwu [1 ]
Li, Yang [1 ]
Wang, Zheng [1 ]
Ding, Kuiling [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 02期
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; SUBSTITUTED ACRYLIC-ACIDS; DIPHOSPHINE LIGANDS; CROSS-COUPLINGS; 1,4-ADDITION; IMPACT;
D O I
10.1039/c3qo00042g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Rh-I complexes of chiral secondary phosphine oxide ligands have been disclosed to be efficient for the catalytic asymmetric hydrogenation of alpha-arylacrylic and beta-arylbut-3-enoic acids, providing the corresponding chiral alpha-arylpropanoic and beta-arylbutanoic acids in excellent yields with up to 97% ee, including several anti-inflammatory drugs.
引用
收藏
页码:155 / 160
页数:6
相关论文
共 64 条
[1]   New class of chiral diphosphine ligands for highly efficient transition metal-catalyzed stereoselective reactions: The bis(diphenylphosphino) five-membered biheteroaryls [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Antognazza, P ;
Cesarotti, E ;
Demartin, F ;
Pilati, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6244-6251
[2]   Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide [J].
Brown, RA ;
Pollet, P ;
McKoon, E ;
Eckert, CA ;
Liotta, CL ;
Jessop, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1254-1255
[3]  
Chan A. S. C., 1991, CHEM ABSTR, V115, P28896
[4]  
Claver C, 2000, CHEM COMMUN, P961
[5]   Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane [J].
Crudden, CM ;
Hleba, YB ;
Chen, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9200-9201
[6]   Catalytic asymmetric Hiyama cross-couplings of racemic α-bromo esters [J].
Dai, Xing ;
Strotman, Neil A. ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3302-+
[7]   Catalytic Asymmetric Hydrogenation of α-CF3- or β-CF3-Substituted Acrylic Acids using Rhodium(I) Complexes with a Combination of Chiral and Achiral Ligands [J].
Dong, Kaiwu ;
Li, Yang ;
Wang, Zheng ;
Ding, Kuiling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14191-14195
[8]   Rh(I)-Catalyzed Enantioselective Hydrogenation of α-Substituted Ethenylphosphonic Adds [J].
Dong, Kaiwu ;
Wang, Zheng ;
Ding, Kuiling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12474-12477
[9]   Enantioselective catalysis with chiral phosphine oxide preligands [J].
Dubrovina, NV ;
Börner, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (44) :5883-5886
[10]   Highly effective soluble polymer-supported catalysts for asymmetric hydrogenation [J].
Fan, QH ;
Ren, CY ;
Yeung, CH ;
Hu, WH ;
Chan, ASC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7407-7408