Journal article

Synthesis of Acyl Phosphoramidates Employing a Modified Staudinger Reaction

Iain Currie, Brad E Sleebs

ORGANIC LETTERS | AMER CHEMICAL SOC | Published : 2021

Abstract

A one-step synthesis of acyl phosphoramidates from a variety of functionalized acyl azides has been developed employing trimethylsilyl chloride as an activating agent in a modified Staudinger reaction. The methodology was further adapted to include the in situ generation of the acyl azides from a diverse selection of carboxylic acids and hydrazide starting synthons. The reaction scope was extended to include the synthesis of imidodiphosphates and the natural product Microcin C.

University of Melbourne Researchers

Grants

Awarded by Australian National Health and Medical Research Council


Funding Acknowledgements

This work was funded by the Australian National Health and Medical Research Council (Development Grant 1135421 to B.E.S.) and the Australian Cancer Research Foundation and the Victorian State Government Operational Infrastructure Support. B.E.S. is a Corin Fellow. We thank Lars Stevens-Cullinane from The Walter and Eliza Hall Institute of Medical Research for acquisition of <SUP>31</SUP>P NMR.