Asymmetric catalysis in the pharmaceutical industry

被引:123
作者
Hawkins, JM [1 ]
Watson, TJN [1 ]
机构
[1] Pfizer Global Res & Dev, Groton, CT 06340 USA
关键词
asymmetric catalysis; chiral auxiliaries; freedom to operate; hydrogenation; industrial processes;
D O I
10.1002/anie.200330072
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The best catalyst from a chemical perspective is not necessarily the best catalyst from an overall economic perspective. In competing approaches to candoxatril the most selective catalyst for the asymmetric hydrogenation (see scheme) was not the one ultimately chosen. The constraints of the pharmaceutical industry are discussed with regard to the application of asymmetric catalysis to the large-scale synthesis of drug candidates and commercial drugs.
引用
收藏
页码:3224 / 3228
页数:5
相关论文
共 27 条
[1]   Large-scale candoxatril asymmetric hydrogenation [J].
Bulliard, M ;
Laboue, B ;
Lastennet, J ;
Roussiasse, S .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (04) :438-441
[2]   Me-DuPHOS-Rh-catalyzed asymmetric synthesis of the pivotal glutarate intermediate for candoxatril [J].
Burk, MJ ;
Bienewald, F ;
Challenger, S ;
Derrick, A ;
Ramsden, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3290-3298
[3]   SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].
CAI, DW ;
PAYACK, JF ;
BENDER, DR ;
HUGHES, DL ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181
[4]   Stereoselective synthesis of a candoxatril intermediate via asymmetric hydrogenation [J].
Challenger, S ;
Derrick, A ;
Mason, CP ;
Silk, TV .
TETRAHEDRON LETTERS, 1999, 40 (11) :2187-2190
[5]   In situ recycling of chiral ligand and surplus nucleophile for a noncatalytic reaction: Amplification of process throughput in the asymmetric addition step of efavirenz (DMP 266) [J].
Choudhury, A ;
Moore, JR ;
Pierce, ME ;
Fortunak, JM ;
Valvis, L ;
Confalone, PN .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :324-328
[6]  
Collet A, 1998, ANGEW CHEM INT EDIT, V37, P3239, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3239::AID-ANIE3239>3.0.CO
[7]  
2-U
[8]  
Collet A., 1998, ANGEW CHEM, V110, P3429
[9]  
COLLUM DB, 1996, 1997 YB SCI FUT, P284
[10]   A CATALYTIC ENANTIOSELECTIVE SYNTHETIC ROUTE TO THE IMPORTANT ANTIDEPRESSANT SERTRALINE [J].
COREY, EJ ;
GANT, TG .
TETRAHEDRON LETTERS, 1994, 35 (30) :5373-5376