A HIGHLY ENANTIOSELECTIVE RHODIUM CATALYST FOR THE HYDROGENATION OF ALIPHATIC ALPHA-KETO ESTERS

被引：23

作者：

SPINDLER, F

PITTELKOW, U

BLASER, HU

机构：

[1] Central Research Services, Ciba-Geigy AG, Basel, CH-4002, R-1060, P.O. Box

来源：

CHIRALITY | 1991年 / 3卷 / 04期

关键词：

ENANTIOSELECTIVE CATALYSIS; (2S)-ETHYL-2-HYDROXY-4-PHENYLBUTYRATE; (S)-ETHYL LACTATE; ALPHA-HYDROXY ESTERS; (2S; 3S)-NORPHOS; RHODIUM DIPHOSPHINE CATALYST;

D O I：

10.1002/chir.530030423

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The enantioselective hydrogenation of several alpha-keto acid derivatives with rhodium diphosphine catalysts has been investigated using a random screening approach. The neutral rhodium catalyst prepared in situ from bis(2,5-norbornadiene rhodium chloride) and NORPHOS has been found to be an excellent catalyst for preparing aliphatic alpha-hydroxy esters in high optical purities. The reaction parameters for the hydrogenation of ethyl 2-oxo-4-phenyl-butyrate, an intermediate for the ACE inhibitor Benazepril, were optimized and the best optical yields obtained were 96%.

引用

页码：370 / 375

页数：6

共 28 条

[11]

HAYASHI T, 1976, TETRAHEDRON LETT, V48, P4351

[12]

HEIL B, 1983, HOMOGENEOUS CATALYSI, P317

[13]

HEIL B, 1985, C SCHORLEMMER LEUNA, V27, P739

[14] NEW PROCEDURE FOR GAS-CHROMATOGRAPHIC ENANTIOMER SEPARATION - APPLICATION TO CHIRAL AMINES AND HYDROXY-ACIDS [J].

KONIG, WA ;

BENECKE, I ;

SIEVERS, S .

JOURNAL OF CHROMATOGRAPHY, 1982, 238 (02) :427-432

[15]

LANDIS CR, 1987, J AM CHEM SOC, V109, P6217, DOI 10.1021/ja00254a602

[16] ASYMMETRIC HYDROGENATION OF METHYL-(Z)-ALPHA-ACETAMIDOCINNAMATE CATALYZED BY (1,2-BIS((PHENYL-ORTHO-ANISOYL)PHOSPHINO)ETHANE)RHODIUM(I) - KINETICS, MECHANISM, AND ORIGIN OF ENANTIOSELECTION [J].

LANDIS, CR ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1746-1754

[17]

MORTREUX A, 1987, B SOC CHIM FR, P631

[18]

NOYORI R, 1989, MOD SYN MET, V5, P115

[19] CHIRAL METAL-COMPLEXES AS DISCRIMINATING MOLECULAR CATALYSTS [J].

NOYORI, R .

SCIENCE, 1990, 248 (4960) :1194-1199

[20]

NOYORI R, 1987, J AM CHEM SOC, V109, P5896

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