141973-58-2Relevant articles and documents
Reaction of azides with trimethyl phosphite in the presence of water: a chemoselective synthesis of functionalized phosphoramidates
Zidani, A.,Carrie, R.,Vaultier, M.
, p. 71 - 75 (2007/10/02)
The reductive phosphorylation of azides with trimethyl phosphite and water in THF leads to the corresponding phosphoramidates which are protected primary amines in excellent yields.The P-N bond in these derivatives may be easily cleft in acidic medium to give the primary amine salts.Some examples are reported.The bis-anion 4 obtained by metallation of 3b is C-alkylated at low temperature leading to new phosphoramidates. 3i and 3j derived from α-azidoketones could not be transformed into the corresponding α-aminoketone salts.The use of methyl diphenylphosphinite in place of trimethyl phosphite leads to the diphenylphosphinamide 7 which, when treated with para-toluenesulfonic acid monohydrate in ether, gives the corresponding α-aminoacetone salt 8 in good yield.Keywords: azides / reductive phosphorylation / phosphoramidates / chemoselective reduction / functionalized primary amines