Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water

被引：177

作者：

Cai, JX ^{[1
]}

Zhou, ZH ^{[1
]}

Zhao, GF ^{[1
]}

Tang, CC ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 26期

关键词：

D O I：

10.1021/ol027197f

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

[GRAPHICS] In homogeneous H2O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield. In this reaction, Me3N, DMAP, DABCO, and urotropine were good catalysts. Except for low-carbon alcohols, tetrahydrofuran, 1,4-dioxane, and acetonitrile could be chosen as the solvent. Under this condition, the diastereoselective reaction of nitrobenzaldehyde and L-menthyl acrylate was realized with 88-99% de.

引用

页码：4723 / 4725

页数：3

共 24 条

[1]

Piperonal as electrophile in the Baylis-Hillman reaction.: A synthesis of hydroxy-β-piperonyl-γ-butyrolactone derivative [J].