Synthesis 2011(19): 3109-3114  
DOI: 10.1055/s-0030-1260176
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalyzed Synthesis of α-(Substituted Methyl)vinylphosphonates

Cécile Garzon, Mireille Attolini*, Michel Maffei*Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille (iSm2), UMR CNRS 6263, équipe HIT, B.P. 551, Campus scientifique de Saint Jérôme, 13397 Marseille Cedex 20, France
Fax: +33(4)91289402; e-Mail: michel.maffei@univ-cezanne.fr; e-Mail: mireille.attolini@univ-cezanne.fr;
Further Information

Publication History

Received 11 May 2011
Publication Date:
18 August 2011 (eFirst)

Abstract

α-(Substituted methyl)vinylphosphonates are obtained by a DABCO-catalyzed substitution reaction of diethyl α-(tert-butoxycarbonyloxymethyl)vinylphosphonate­ and (N-protected) amino- or soft pronucleophiles. The reactions are easily performed under mild conditions (r.t., 1 h), and give good to excellent yields of the title compounds. A diphosphonate by-product was isolated in some examples, when the nucleophile has a less pronounced nucleophilic character.