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3103975 
Journal Article 
REACTION OF AZIDES WITH TRIMETHYL PHOSPHITE IN THE PRESENCE OF WATER - A CHEMOSELECTIVE SYNTHESIS OF FUNCTIONALIZED PHOSPHORAMIDATES 
Zidani, A; Carrie, R; Vaultier, M 
1992 
Yes 
Bulletin de la Société Chimique de Paris
ISSN: 0037-8968 
129 
1 
71-75 
WOS:A1992HN89400010 
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 alpha-azidoketones could not be transformed into the corresponding alpha-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 alpha-aminoacetone salt 8 in good yield. 
AZIDES; REDUCTIVE PHOSPHORYLATION; PHOSPHORAMIDATES; CHEMOSELECTIVE REDUCTION; FUNCTIONALIZED PRIMARY AMINES