Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis

被引：125

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

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 14期

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

页码：2421 / 2424

页数：4

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
ACHIWA, K
[J]. CHEMISTRY LETTERS, 1977, (07) : 777 - 778
[2] ENZYMATIC ESTERIFICATION OF 1-FERROCENYLETHANOL - AN ALTERNATE APPROACH TO CHIRAL FERROCENYL BIS-PHOSPHINES
BOAZ, NW
[J]. TETRAHEDRON LETTERS, 1989, 30 (16) : 2061 - 2064
[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
CESAROTTI, E
CHIESA, A
CIANI, G
SIRONI, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 251 (01) : 79 - 91
[7] UNUSUAL AMINO-ACIDS .4. ASYMMETRIC-SYNTHESIS OF THIENYLALANINES
DOBLER, C
KREUZFELD, HJ
KRAUSE, HW
MICHALIK, M
[J]. 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
FIORINI, M
GIONGO, GM
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1979, 5 (04): : 303 - 310
[9] ASYMMETRIC SYNTHESIS - PRODUCTION OF OPTICALLY-ACTIVE AMINO-ACIDS BY CATALYTIC-HYDROGENATION
FRYZUK, MD
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (19) : 6262 - 6267
[10] PREPARATION AND RESOLUTION OF N,N-DIMETHYL-ALPHA-FERROCENYLETHYLAMINE ADVANCED ORGANIC EXPERIMENT
GOKEL, GW
UGI, IK
[J]. JOURNAL OF CHEMICAL EDUCATION, 1972, 49 (04) : 294 - &

← 1 2 3 →