Organocatalyzed Synthesis of α-(Substituted Methyl)vinylphosphonates

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.

Key words

α-(substituted methyl)vinylphosphonates - organocatalysis - diethyl α-(tert-butoxycarbonyloxymethyl)vinylphosphonate - pronucleophiles - 1,4-diazabicyclo[2.2.2]octane

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