在水存在的情况下，均相介质中Baylis-Hillman反应的速率急剧加速。

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

作者信息

Cai Juexiao, Zhou Zhenghong, Zhao Guofeng, Tang Chuchi

机构信息

State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

出版信息

Org Lett. 2002 Dec 26;4(26):4723-5. doi: 10.1021/ol027197f.

DOI:10.1021/ol027197f

PMID:12489971

Abstract

[reaction: see text] In homogeneous H(2)O/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, Me(3)N, 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.

摘要

[反应：见正文] 在均相水/溶剂介质中，芳香醛与丙烯腈或丙烯酸酯的反应速率大大加快，这使得反应时间缩短、反应温度降低且产率提高。在该反应中，三甲胺、4-二甲氨基吡啶、1,4-二氮杂双环[2.2.2]辛烷和乌洛托品是良好的催化剂。除低碳醇外，四氢呋喃、1,4-二氧六环和乙腈可作为溶剂。在此条件下，实现了硝基苯甲醛与L-薄荷基丙烯酸酯的非对映选择性反应，非对映体过量值为88 - 99%。