Enantioselective Rh-catalyzed hydrogenation of vinyl carboxylates with monodentate phosphite ligands

被引:80
作者
Reetz, MT [1 ]
Goossen, LJ [1 ]
Meiswinkel, A [1 ]
Paetzold, J [1 ]
Jensen, JF [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/ol035076p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkyl-substituted vinylcarboxylates, which normally show poor enantioselectivity in Rh-catalyzed hydrogenation with traditional chiral diphosphines, undergo highly enantioselective reactions with BINOL- and carbohydrate-based monophosphite ligands.
引用
收藏
页码:3099 / 3101
页数:3
相关论文
共 32 条
[1]  
[Anonymous], ANGEW CHEM
[2]  
[Anonymous], ANGEW CHEM
[3]   Asymmetric hydrogenation of acyclic enol esters [J].
Boaz, NW .
TETRAHEDRON LETTERS, 1998, 39 (31) :5505-5508
[4]   Utilization of an industrial feedstock without separation - Ruthenium-catalysed hydrocarboxylation of propadiene and propyne [J].
Bruneau, C ;
Neveux-Duflos, M ;
Dixneuf, PH .
GREEN CHEMISTRY, 1999, 1 (04) :183-185
[5]   C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519
[6]   Enantioselective hydrogenation with inexpensive, easily available monodentate phosphite ligands [J].
Chen, WP ;
Xiao, JL .
TETRAHEDRON LETTERS, 2001, 42 (15) :2897-2899
[7]   Synthesis of novel chiral binaphthyl phosphorus ligands and their applications in Rh-catalyzed asymmetric hydrogenation [J].
Chi, YX ;
Zhang, XM .
TETRAHEDRON LETTERS, 2002, 43 (27) :4849-4852
[8]   STEREOSELECTIVE SYNTHESIS OF Z-ENOL ESTERS CATALYZED BY [BIS(DIPHENYLPHOSPHINO)ALKANE]BIS(2-METHYLPROPENYL)RUTHENIUM COMPLEXES [J].
DOUCET, H ;
HOFER, J ;
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :850-851
[9]   GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES [J].
DOUCET, H ;
MARTINVACA, B ;
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7247-7255
[10]   Powerful control by organoruthenium catalysts of the regioselective addition to C(1) or C(2) of the prop-2-ynyl ethers CC triple bond [J].
Doucet, H ;
Derrien, N ;
Kabouche, Z ;
Bruneau, C ;
Dixneuf, PH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 551 (1-2) :151-157