STEREOSELECTIVE REDUCTION OF 2-METHYL-3-OXO ESTERS (OR AMIDES) WITH SODIUM-BOROHYDRIDE CATALYZED BY MANGANESE(II) CHLORIDE OR TETRABUTYLAMMONIUM BOROHYDRIDE - A PRACTICAL PREPARATION OF ERYTHRO AND THREO-3-HYDROXY-2-METHYL ESTERS (OR AMIDES)

被引：50

作者：

TANIGUCHI, M ^{[1
]}

FUJII, H ^{[1
]}

OSHIMA, K ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DIV MAT CHEM,SAKYO KU,KYOTO 60601,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(01)81804-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

erythro-3-Hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 2-methyl-3-oxo esters or 2-methyl-3-oxo amides in the presence of a catalytic amount of manganese(II) chloride. On the other hand, reduction of these substrates with n-Bu(4)NBH(4) provided threo-isomers selectively. erythro-Selective reduction of 2-methyl-3-oxo amides with NaBH3CN in 1N HCl-MeOH is also described.

引用

页码：11169 / 11182

页数：14

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