Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis

被引:128
作者
Boaz, NW [1 ]
Debenham, SD [1 ]
Mackenzie, EB [1 ]
Large, SE [1 ]
机构
[1] Eastman Chem Co, Res Labs, Kingsport, TN 37662 USA
关键词
D O I
10.1021/ol0261736
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new series of ligands with a novel phosphine-aminophosphine ligation design as depicted in structure 1 has been prepared on a ferrocenylethyl backbone. These BoPhoz ligands of structure 2 have afforded exceedingly high activity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of dehydro-alpha-amino acid derivatives, itaconic acids, and alpha-ketoesters. These air-stable ligands are readily prepared from cost-effective and non-pyrophoric intermediates.
引用
收藏
页码:2421 / 2424
页数:4
相关论文
共 28 条
[1]   ASYMMETRIC REACTIONS CATALYZED BY TRANSITION-METAL COMPLEXES .2. NEW CHIRAL PHOSPHINE RHODIUM CATALYSTS FOR ASYMMETRIC SYNTHESIS OF (R)-N-BENZYLOXYCARBONYLANINE AND (S)-N-BENZYLOXYCARBONYLALANINE [J].
ACHIWA, K .
CHEMISTRY LETTERS, 1977, (07) :777-778
[3]  
BRIEDEN W, 1998, Patent No. 5760264
[4]  
Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121
[5]  
CASULNUOVO AL, 1994, J AM CHEM SOC, V116, P9869
[6]   ASYMMETRIC HYDROGENATION CATALYZED BY AMINOPHOSPHINE-PHOSPHINITERHODIUM COMPLEXES DERIVED FROM NATURAL AMINOALCOHOLS AND X-RAY CRYSTAL-STRUCTURE OF (1,5-CYCLOOCTADIENE)-(S)-N-(DIPHENYLPHOSPHINO)-2-DIPHENYLPHOSPHINOXYMETHYLPYRROLIDINERHODIUM(I) PERCHLORATE [J].
CESAROTTI, E ;
CHIESA, A ;
CIANI, G ;
SIRONI, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 251 (01) :79-91
[7]   UNUSUAL AMINO-ACIDS .4. ASYMMETRIC-SYNTHESIS OF THIENYLALANINES [J].
DOBLER, C ;
KREUZFELD, HJ ;
KRAUSE, HW ;
MICHALIK, M .
TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1833-1842
[8]   AMINOPHOSPHINE-RHODIUM COMPLEXES AS CATALYSTS IN ASYMMETRIC HYDROGENATION - DEPENDENCE OF THE ENANTIOSELECTIVITY ON THE STRUCTURE OF THE CHIRAL LIGANDS [J].
FIORINI, M ;
GIONGO, GM .
JOURNAL OF MOLECULAR CATALYSIS, 1979, 5 (04) :303-310
[9]   ASYMMETRIC SYNTHESIS - PRODUCTION OF OPTICALLY-ACTIVE AMINO-ACIDS BY CATALYTIC-HYDROGENATION [J].
FRYZUK, MD ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (19) :6262-6267
[10]   PREPARATION AND RESOLUTION OF N,N-DIMETHYL-ALPHA-FERROCENYLETHYLAMINE ADVANCED ORGANIC EXPERIMENT [J].
GOKEL, GW ;
UGI, IK .
JOURNAL OF CHEMICAL EDUCATION, 1972, 49 (04) :294-&