Tetrahedron

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 …

B List, A Doehring, MTH Fonseca, A Job, RR Torres

Index: List, Benjamin; Doehring, Arno; Hechavarria Fonseca, Maria T.; Job, Andreas; Rios Torres, Ramon Tetrahedron, 2006 , vol. 62, # 2-3 p. 476 - 482

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Citation Number: 68

Abstract

We describe a highly efficient new methodology for the synthesis of (E)-α, β-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 ...