Organocatalyzed Synthesis of α-(Substituted Methyl)vinylphosphonates
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.
α-(substituted methyl)vinylphosphonates - organocatalysis - diethyl α-(tert-butoxycarbonyloxymethyl)vinylphosphonate - pronucleophiles - 1,4-diazabicyclo[2.2.2]octane