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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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

2005; Elsevier BV; Volume: 62; Issue: 2-3 Linguagem: Inglês

10.1016/j.tet.2005.09.081

ISSN

1464-5416

Autores

Benjamin List, A. Doehring, Maria T. Hechavarria Fonseca, Andreas Job, Ramón Rios,

Tópico(s)

Phosphorus compounds and reactions

Resumo

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 ingredients, is described.

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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