New efficient catalysts for enantioselective transfer hydrogenations

被引:100
作者
Puntener, K [1 ]
Schwink, L [1 ]
Knochel, P [1 ]
机构
[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY
关键词
D O I
10.1016/0040-4039(96)01853-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New C-2-symmetrical diaminoferrocenyl derivatives 3 and 2-amino(sulfonamido)cyclohexanes 4 were found to be highly active ligands for the ruthenium catalyzed asymmetric transfer hydrogenation of ketones. Contrary to many existing catalytic systems, the ligands 3 show a high activity at 25 degrees C and operate even at -30 degrees C (up to 90 % ee). On the other hand, the slightly less active ligands 4 are very easily prepared and are highly enantioselective at 30 degrees C in HCOOH/Et(3)N (up to 96 % ee). Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:8165 / 8168
页数:4
相关论文
共 20 条
[1]   ASYMMETRIC CATALYSIS .52. RHODIUM CATALYZED ENANTIOSELECTIVE TRANSFER HYDRATION OF C=C DOUBLE-BONDS WITH THE HCO2H/NET3 SYSTEM AS A HYDROGEN SOURCE [J].
BRUNNER, H ;
LEITNER, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 387 (02) :209-217
[2]   ASYMMETRIC CATALYZES .31. ENANTIOSELECTIVE CATALYTIC REDUCTION OF DEHYDRO AMINO-ACIDS WITH FORMIC-ACID [J].
BRUNNER, H ;
KUNZ, M .
CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (09) :2868-2873
[3]   EFFICIENT RUTHENIUM-CATALYZED TRANSFER HYDROGENATION OF KETONES BY PROPAN-2-OL [J].
CHOWDHURY, RL ;
BACKVALL, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1063-1064
[4]   A CHIRAL SAMARIUM-BASED CATALYST FOR THE ASYMMETRIC MEERWEIN-PONNDORF-VERLEY REDUCTION [J].
EVANS, DA ;
NELSON, SG ;
GAGNE, MR ;
MUCI, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9800-9801
[5]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522
[6]   ASYMMETRIC CATALYTIC REDUCTION OF CARBONYL-COMPOUNDS USING C-2 SYMMETRICAL DIAMINES AS CHIRAL LIGANDS [J].
GAMEZ, P ;
FACHE, F ;
LEMAIRE, M .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :705-718
[7]   A ruthenium(II) complex with a C-2-symmetric diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones [J].
Gao, JX ;
Ikariya, T ;
Noyori, R .
ORGANOMETALLICS, 1996, 15 (04) :1087-1089
[8]  
GOKEL GW, 1972, J ORG CHEM, V37, P3052, DOI 10.1021/jo00985a002
[9]   ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES [J].
HASHIGUCHI, S ;
FUJII, A ;
TAKEHARA, J ;
IKARIYA, T ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7562-7563
[10]  
HERRMANN R, 1986, LIEBIGS ANN CHEM, P251