T. Wada et al., A CONVENIENT METHOD FOR PHOSPHORYLATION INVOLVING A FACILE OXIDATION OF H-PHOSPHONATE MONOESTERS VIA BIS(TRIMETHYLSILYL) PHOSPHITES, Tetrahedron letters, 39(39), 1998, pp. 7123-7126
A new convenient route to phosphate monoesters from alcohols has been
developed. H-Phosphonate monoesters, which are readily accessible by p
hosphonylation of the parent alcohols, were oxidized with t-BuOOH or N
-sulfonyloxaziridines under anhydrous conditions via the corresponding
bis(trimethylsilyl) phosphites. N,O-Bis(trimethylsilyl)benzamide (BSB
) and (camphorsulfonyl)oxaziridine (CSO) were found to be highly effec
tive for silylation of H-phosphonates and oxidation of silyl phosphite
s, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.