Diethyl phosphonomethyl triflate

The related planar pyrrole analog 118 has also been prepared (2) from either ethyl or benzyl pyrrole-2-carboxylate 116. Direct alkylation with diethyl phosphonomethyl triflate (70) and base produced the N-phosphonomethylpyrrole 2-carboxylate 117, which was deprotected with trimethylsilyl bromide and saponified to the corresponding phosphonic acid 118. 

The successful synthesis of diethyl phosphonomethyl triflate (193) is possible only at -15°C at higher temperatures formation of the ether (194) becomes important and exemplifies... 

An unusual electrophilic phosphonomethylation using diethyl phosphonomethyltridatc has been reported. " A protected analogue of 3-dcoxy-D-mflnno-2-octulosonic acid is metallated in the anomeric position at low temperature in THF and then reacted with diethyl phosphonomethyl-triflate to give the phosphonylated (i-C-glycosyl derivative in 50% yield. ... 

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