Synthesis of Acyl Phosphoramidates Employing a Modified Staudinger Reaction

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.

Automated summary

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