Synthesis of a Series of γ-Keto Allyl Phosphonates.

J Org Chem

Université de Tunis El Manar , Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisia.

Published: March 2016

Under solvent-free conditions and at 80 °C, a DMAP- or imidazole-mediated clean and rapid conversion of cyclic Morita-Baylis-Hillman (MBH) acetates into the corresponding γ-keto allyl phosphonates in 70-93% yields is described herein. This allylic nucleophilic substitution works well with primary and secondary acetates bearing, at the β'-position, linear or branched alkyl groups and aryl groups.

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http://dx.doi.org/10.1021/acs.joc.5b02106DOI Listing

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