A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β-unsaturated esters from aldehydes
A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β-unsaturated esters from aldehydes
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DOI：
10.1016/j.tet.2005.09.081
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发表时间：
2006-01-09
期刊：
影响因子：
2.1
通讯作者：
Torres, RR
中科院分区：
文献类型：
--
作者：
List, B;Doehring, A;Torres, RR
我们描述了一种由醛合成（E）-α，β-不饱和酯的高效新方法。在我们的DMAP催化的反应中，如果用市售的或合成上容易获得的丙二酸半酯处理，芳香族和脂肪族醛都高度区域选择性和立体选择性地提供所需的产物。本文介绍了对甲氧基肉桂酸酯作为防晒剂的合成方法。(c)2005爱思唯尔有限公司保留所有权利。
We describe a highly efficient new methodology for the synthesis of (E)-alpha,beta-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described. (c) 2005 Elsevier Ltd. All rights reserved.