TIN(II) CHLORIDE CATALYZED ADDITION OF DIAZO SULFONES, DIAZO PHOSPHINE OXIDES, AND DIAZO PHOSPHONATES TO ALDEHYDES

被引：90

作者：

HOLMQUIST, CR ^{[1
]}

ROSKAMP, EJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 09期

基金：

美国国家卫生研究院;

关键词：

TIN(II) CHLORIDE; CATALYST; BETA-KETO SULFONES; BETA-KETO PHOSPHINE OXIDES; AND BETA-KETO PHOSPHONATES;

D O I：

10.1016/S0040-4039(00)91877-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diazo sulfones, diazo phosphine oxides, and diazo phosphonates add to aldehydes in the presence of a catalytic amounts of tin(II) chloride to yield beta-keto sulfones, beta-keto phosphine oxides, and beta-keto phosphonates, respectively. Reactions with primary aldehydes proceed in higher yields, 53-79%, than those of secondary aldehydes, 42-56%. Reactions with tertiary aldehydes, which are more sterically encumbered substrates, give only 5-36% yields.

引用

页码：1131 / 1134

页数：4

共 22 条

[1] QUASI-QUANTITATIVE PREPARATION OF BETA-CARBONYL PHOSPHONATES BY THE USE OF A RELAY BASE, LDA ((I-C3H7)2NLI] [J].