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Reliable and Versatile Synthesis of 2-Aryl-Substituted Cinnamic Acid Esters

Alen Ianni, Siegfried R. Waldvogel*

*Rheinische Friedrich-Wilhelms-Universität Bonn, Kekulé-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Straße 1, 53121 Bonn, Email:

A. Ianni, S. R. Waldvogel, Synthesis, 2006, 2103-2112.

DOI: 10.1055/s-2006-942404


2-Aryl-substituted phosphono acetates can be readily synthesized by a four-step sequence from the respective arenes. Succeeding Horner-Wadsworth-Emmons olefinations provide stereoselectively the 2-aryl cinnamic acid esters even when sensitive moieties are involved.

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Key Words

bromination, phosphorylation, olefination, Friedel-Crafts acylation, Arbuzov reaction, Wittig-Horner reaction, sodium borohydride

ID: J66-Y2006-1910