Synthesis of new chiral diphosphine ligand (BisbenzodioxanPhos) and its application in asymmetric catalytic hydrogenation

被引:66
作者
Pai, CC [1 ]
Li, YM
Zhou, ZY
Chan, ASC
机构
[1] Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Design & Synth, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
关键词
BisbenzodioxanPhos; hydrogenation; beta-keto esters; naproxen;
D O I
10.1016/S0040-4039(02)00383-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The new chiral diphosphine ligand [(5.6) (5'.6')-bis(1.2-ethylenedioxy)biphenyl-2.2'-diyl]bis(diphenylphosphine) (Bisben-zodioxanPhos) has been successfully prepared and used in ruthenium-catalyzed asymmetric hydrogenation of 2-(6'-methoxy-2'-naphthyl)propenoic acid and beta-keto esters with high enantioselectivity (92.2% and up to 99.5% ee. respectively). (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:2789 / 2792
页数:4
相关论文
共 28 条
[1]   Chiral atropisomeric five-membered biheteroaromatic diphosphines: New ligands of the bibenzimidazole and biindole series [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Antognazza, P ;
Cesarotti, E ;
Demartin, F ;
Pilati, T ;
Zotti, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :445-453
[2]   (DIPHENYLPHOSPHINO)-BIHETEROARYLS - THE FIRST EXAMPLE OF A NEW CLASS OF CHIRAL ATROPISOMERIC CHELATING DIPHOSPHINE LIGANDS FOR TRANSITION-METAL-CATALYZED STEREOSELECTIVE REACTIONS [J].
BENINCORI, T ;
BRENNA, E ;
SANNICOLO, F ;
TRIMARCO, L ;
ANTOGNAZZA, P ;
CESAROTTI, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) :685-686
[3]   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
[4]  
BIERNACKI W, 1980, POL J CHEM, V54, P2239
[5]  
Chan A., 1991, U.S. Patent, Patent No. 4994607
[6]   Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes [J].
Chan, ASC ;
Zhang, FY ;
Yip, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :4080-4081
[7]  
CHAN ASC, 1992, Patent No. 5144050
[8]  
Fanat P. E., 1974, SYNTHESIS-STUTTGART, P9
[9]  
Gelpke AES, 1999, CHEM-EUR J, V5, P2472
[10]   Twenty years of naproxen technology [J].
Harrington, PJ ;
Lodewijk, E .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (01) :72-76