DIRECT CONVERSION OF ESTERS TO SECONDARY AMIDES USING TIN(II) REAGENTS

被引：10

作者：

WANG, WB ^{[1
]}

RESTITUYO, JA ^{[1
]}

ROSKAMP, EJ ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)79291-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed two new procedures for the direct conversion of esters to secondary amides. In our first procedure, secondary amides can be prepared in 83-98% yield starting from glycol esters. Addition of Sn[N(TMS)2]2 and a primary amine to the glycol ester generates an intermediate tin(II) alkoxy amide, which delivers the amino group intramolecularly to give the amide. A second general procedure for the preparation of secondary amides starts with methyl esters. Treatment of methyl esters with a tin reagent derived from Sn[N(TMS)2]2, Me2NCH2CH2OH, and a primary amine yields secondary amides in 87-98% yield.

引用

页码：7217 / 7220

页数：4

共 6 条

[1] CHEMICALLY LABILE STANNYLENE-NITROGEN BONDS - THE CHEMOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF N,N-BIS(TRIMETHYLSILYL)ENAMINES AND N,N-DIALKYLENAMINES [J].