Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina

被引：86

作者：

Borszeky, K ^{[1
]}

Mallat, T ^{[1
]}

Baiker, A ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,DEPT CHEM ENGN & IND CHEM,ETH ZENTRUM,CH-8092 ZURICH,SWITZERLAND

来源：

CATALYSIS LETTERS | 1996年 / 41卷 / 3-4期

关键词：

enantioselective; hydrogenation; cinchonidine; Pd/alumina; methylpentenoic acid;

D O I：

10.1007/BF00811491

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A chiral alkanoic acid was prepared with up to 52% excess of the (S) enantiomer by hydrogenating alpha,beta-unsaturated carboxylic acid with a cinchonidine-Pd/Al2O3 catalyst system. Favourable conditions are: high surface hydrogen concentration (greater than or equal to 60 bar hydrogen pressure, low catalyst concentration and apolar solvents), near ambient temperature and a cinchonidine/reactant molar ratio of at least 0.4 mol%. It is proposed that high hydrogen solubility and the presence of 2-methyl-2-pentenoic acid reactant as dimers are advantageous for enantiodifferentiation.

引用

页码：199 / 202

页数：4

共 23 条

[1]

ALBERT SCC, 1993, CHEMTECH, P46

[2]

ALCORN WR, 1984, CATALYSIS ORGANIC RE, V18, P221

[3] 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

[4] 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

[5]

BLASER HU, 1993, STUD SURF SCI CATAL, V78, P139

[6] ENANTIOSELECTIVE SYNTHESIS USING CHIRAL HETEROGENEOUS CATALYSTS [J].

BLASER, HU .

TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :843-866

[7]

CORMA A, 1993, STUD SURF SCI CATAL, V75, P2293

[8] DISTAL RENAL TUBULAR-ACIDOSIS SYNDROMES - A PATHOPHYSIOLOGICAL APPROACH [J].

HALPERIN, ML ;

GOLDSTEIN, MB ;

RICHARDSON, RMA ;

STINEBAUGH, BJ .

AMERICAN JOURNAL OF NEPHROLOGY, 1985, 5 (01) :1-8

[9]

KAGAN HB, 1988, B SOC CHIM FR, V5, P846

[10] ENANTIOSELECTIVE HYDROGENATION OF ETHYL PYRUVATE - INFLUENCE OF OXIDATIVE TREATMENT OF CINCHONIDINE-MODIFIED PLATINUM CATALYST AND HEMIKETAL FORMATION IN ALCOHOLIC SOLVENTS [J].

MINDER, B ;

MALLAT, T ;

SKRABAL, P ;

BAIKER, A .

CATALYSIS LETTERS, 1994, 29 (1-2) :115-124

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