Synthesis 2011(19): 3109-3114  
DOI: 10.1055/s-0030-1260176
© 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
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Further Information

Publication History

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


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.