A convenient method for phosphorylation involving a facile oxidation of H-Phosphonate monoesters via bis(trimethylsilyl) phosphites

✍ Scribed by Takeshi Wada; Akira Mochizuki; Yuichi Sato; Mitsuo Sekine

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 300 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01513-5

✦ Synopsis

A new convenient route to phosphate monoesters from alcohols has been developed. H-Phosphonate monoesters, which are readily accessible by phosphonylation 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 effective for silylation of H-phosphonates and oxidation of silyl phosphites, respectively.