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

Benjamin List, Arno Doehring, Maria T. Hechavarria Fonseca, Andreas Job, Ramon Rios Torres

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

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 ingredients, is described.

Original languageBritish English
Pages (from-to)476-482
Number of pages7
JournalTetrahedron
Volume62
Issue number2-3
DOIs
StatePublished - 9 Jan 2006

Keywords

  • α,β-Unsaturated esters
  • (E)-Stereoselectivity
  • DMAP-catalysis
  • Doebner-Knoevenagel reaction

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