The resolution of important pharmaceutical building blocks by palladium-catalyzed aerobic oxidation of secondary alcohols

被引:47
作者
Caspi, DD [1 ]
Ebner, DC [1 ]
Bagdanoff, JT [1 ]
Stoltz, BM [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synth, Pasadena, CA 91125 USA
关键词
asymmetric catalysis; kinetic resolution; oxidation; oxygen; palladium; pharmaceutical substance;
D O I
10.1002/adsc.200303188
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The palladium-catalyzed aerobic oxidative kinetic resolution of key pharmaceutical building blocks is described. Substrates investigated are relevant to the enantioselective preparation of Prozac((R)), Singulair((R)), and the promising hNK-1 receptor antagonist from Merck. The latter provides the most selective aerobic oxidative kinetic resolution yet described.
引用
收藏
页码:185 / 189
页数:5
相关论文
共 19 条
[1]   Pd-catalyzed kinetic resolution of benzylic alcohols:: a practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides [J].
Ali, IS ;
Sudalai, A .
TETRAHEDRON LETTERS, 2002, 43 (31) :5435-5436
[2]   Palladium-catalyzed oxidative kinetic resolution with ambient air as the stoichiometric oxidation gas [J].
Bagdanoff, JT ;
Stoltz, BM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (03) :353-357
[3]   Palladium-catalyzed enantioselective oxidation of alcohols:: A dramatic rate acceleration by Cs2CO3/t-BuOH [J].
Bagdanoff, JT ;
Ferreira, EM ;
Stoltz, BM .
ORGANIC LETTERS, 2003, 5 (06) :835-837
[4]  
Bhupathy M., 1995, WO, Patent No. 9518107
[5]  
Bhupathy M., 1997, US Patent, Patent No. 5614632
[6]   Expeditious synthesis of tri-substituted cyclopentane derivatives [J].
Desai, RC ;
Cicala, P ;
Meurer, LC ;
Finke, PE .
TETRAHEDRON LETTERS, 2002, 43 (26) :4569-4570
[7]   Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles [J].
Ferreira, EM ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9578-9579
[8]   The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen [J].
Ferreira, EM ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7725-7726
[9]   Palladium-catalyzed enantioselective oxidations of alcohols using molecular oxygen [J].
Jensen, DR ;
Pugsley, JS ;
Sigman, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7475-7476
[10]   AN EFFICIENT SYNTHESIS OF LTD4 ANTAGONIST L-699,392 [J].
KING, AO ;
CORLEY, EG ;
ANDERSON, RK ;
LARSEN, RD ;
VERHOEVEN, TR ;
REIDER, PJ ;
XIANG, YB ;
BELLEY, M ;
LEBLANC, Y ;
LABELLE, M ;
PRASIT, P ;
ZAMBONI, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3731-3735