ASYMMETRIC-SYNTHESIS - PRACTICAL PRODUCTION OF D-THREONINE AND L-THREONINE - DYNAMIC KINETIC RESOLUTION IN RHODIUM AND RUTHENIUM CATALYZED HYDROGENATION OF 2-ACYLAMINO-3-OXOBUTYRATES

被引：114

作者：

GENET, JP

PINEL, C

MALLART, S

JUGE, S

THORIMBERT, S

LAFFITTE, JA

机构：

[1] Laboratoire de Synthèse Organique, Associé au C.N.R.S., Ecole Nationale Supérieure de Chimie de Paris, 75231 Paris Cedex 05, 11, rue Pierre et Marie Curie

[2] Département Chimie Fine et Bioconversions, G.R.L. (Elf Aquitaine)

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)86108-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective syntheses of D and L threonine are described. Racemic methyl and ethyl 2-acylamino-3-oxobutyrate 1 were synthesized from the corresponding acetoacetates 6 and then hydrogenated stereoselectively via dynamic kinetic resolution with various chiral P * P Rh (I) 8 and Ru (II) 10 catalysts to give syn optically active alcohols which could be converted by hydrolysis and treatment with propylene oxide into threonine. The best results were obtained using (-) CHIRAPHOS Ru and (+) BINAP Ru as catalysts, in the hydrogenation step leading respectively to D threonine (ee: 99 %) and L threonine (ee: 94 %) in 26-34 % overall yields.

引用

页码：555 / 567

页数：13

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