Fluoride-catalyzed aldol reaction of ethyl trimethylsilyldiazoacetate with aldehydes leading to ethyl α-diazo-β-hydroxy esters and rhodium catalyzed decarboxylative rearrangement of diazo urethanes leading to β-amino acrylates

被引：18

作者：

Kanemasa, S ^{[1
]}

Araki, T

Kanai, T

Wada, E

机构：

[1] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Dept Mol Sci & Technol, Kasuga, Fukuoka 8168580, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(99)00933-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl trimethylsilyldiazoacetate reacts smoothly with a variety of aldehydes at 0 degrees C in the presence of a catalytic amount of tetrabutylammonium fluoride to produce alpha-diazo-beta-hydroxy esters in good to excellent yields. The resulting alpha-diazo-beta-hydroxy esters can be,stereoselectively transformed, by a sequence of carbamation with p-toluenesulfonyl isocyanate and rhodium(II)-induced decarboxylative rearrangement, to alpha- or beta-substituted beta-(p-toluenesulfonylamino)acrylates depending upon migration aptitude of the substituents derived from the aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5059 / 5062

页数：4

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