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A convenient method for phosphorylation involving a facile oxidation ofH-Phosphonate monoestersviabis(trimethylsilyl) phosphites

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
39
Identifiers
DOI: 10.1016/s0040-4039(98)01513-5
Keywords
  • Phosphorylation
  • Oxidation
  • Oxaziridines
  • Nucleic Acids

Abstract

Abstract 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.

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