1380066-23-8Relevant articles and documents
[2,3]-Sigmatropic rearrangement of ynamides: Preparation of α-amino allenephosphonates
Gomes, Filipe,Fadel, Antoine,Rabasso, Nicolas
experimental part, p. 5439 - 5444 (2012/09/07)
α-Amino allenephosphonates were easily prepared in two steps from protected amines, propargyl alcohols, and chlorophosphites. First, ynamides were synthesized from unprotected 1-bromopropargyl alcohols using a copper(II) catalyzed coupling reaction. In the second step, the previously prepared ynamides were transformed directly to allenes through a [2,3]-sigmatropic rearrangement of propargyl phosphites. This efficient method led to the formation of a series of α-amino allenephosphonates with diverse substituents on the amine, the phosphonate, and the allene moieties.