Enantioselective hydrogenation of alpha,beta-unsaturated acids. Substrate-modifier interaction over cinchonidine modified Pd/Al2O3

被引:95
作者
Borszeky, K [1 ]
Mallat, T [1 ]
Baiker, A [1 ]
机构
[1] ETH ZENTRUM, SWISS FED INST TECHNOL, DEPT CHEM ENGN & IND CHEM, CH-8092 ZURICH, SWITZERLAND
关键词
D O I
10.1016/S0957-4166(97)00526-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
X-Ray diffraction, IR measurements and catalytic hydrogenation of various substituted acrylic acids in apolar solvents, as well as molecular modelling provide new insight into the nature of the cinchonidine-substrate interaction and a general rule to predict the major enantiomer. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3745 / 3753
页数:9
相关论文
共 35 条
[1]   KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2] [J].
ASHBY, MT ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :589-594
[2]   ACID BASE REACTIONS IN NON-DISSOCIATING SOLVENTS - ACETIC ACID AND TRIETHYLAMINE IN CARBON TETRACHLORIDE AND CHLOROFORM [J].
BARROW, GM ;
YERGER, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (20) :5211-5216
[3]   HOMOGENEOUS AND HETEROGENEOUS CATALYTIC ASYMMETRIC REACTIONS .4. HYDROGENATION OF THE NI COMPLEXES OF CINNAMIC ACID SALTS OVER MRNI CATALYST [J].
BARTOK, M ;
WITTMANN, G ;
BARTOK, GB ;
GONDOS, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 384 (03) :385-395
[4]   AMINO PHOSPHONIC ACIDS .2. AMINOALKYLPHOSPHONIC ACIDS [J].
BERRY, JP ;
ISBELL, AF ;
HUNT, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) :4396-4399
[5]   THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].
BLASER, HU .
CHEMICAL REVIEWS, 1992, 92 (05) :935-952
[6]   ENANTIOSELECTIVE HYDROGENATION .4. HYDROGEN ISOTOPE-EXCHANGE IN 10,11-DIHYDROCINCHONIDINE AND IN QUINOLINE CATALYZED BY PLATINUM-GROUP METALS [J].
BOND, G ;
WELLS, PB .
JOURNAL OF CATALYSIS, 1994, 150 (02) :329-334
[7]   Enantioselective hydrogenation of pyruvic acid oxime to alanine on Pd/alumina [J].
Borszeky, K ;
Mallat, T ;
Aeschiman, R ;
Schweizer, WB ;
Baiker, A .
JOURNAL OF CATALYSIS, 1996, 161 (01) :451-458
[8]   Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina [J].
Borszeky, K ;
Mallat, T ;
Baiker, A .
CATALYSIS LETTERS, 1996, 41 (3-4) :199-202
[9]   THE INFRA-RED ABSORPTION BANDS ASSOCIATED WITH THE COOH AND COOD GROUPS IN DIMERIC CARBOXYLIC ACID .2. THE REGION FROM 3700 TO 1500 CM-1 [J].
BRATOZ, S ;
HADZI, D ;
SHEPPARD, N .
SPECTROCHIMICA ACTA, 1956, 8 (4-5) :249-261
[10]  
CHAN ASC, 1993, CHEMTECH, V23, P46