PAPER	Synthesis 2006: 2103-2112   DOI: 10.1055/s-2006-942404
© Georg Thieme Verlag Stuttgart · New York
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, Germany Fax: +49(228)739608; e-Mail: waldvogel@uni-bonn.de;
Received 9 March 2006

Abstract

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.

Key words

olefination - phosphorylation - acylation - Arbuzov reaction - Horner-Wadsworth-Emmons reaction