New Staudinger Strategy Enabled N -Acyl Phosphinamidites Synthesis

Abstract

A new Staudinger strategy which goes via a unique C-P bond cleavage instead of N-P bond cleavage during the construction of N-acyl phosphinamidites by using acyl-phosphine substrates. The reaction is performed under very mild conditions, with no need for additional catalysts or additives, and thus preserves stereogenic centers that are sensitive to epimerization. A range of novel N-acyl phosphinamidites, including those bearing a chiral amino acid skeleton, axial chirality as well as complex natural product scaffolds were produced with N 2 gas as the only byproduct. These N-acyl phosphinamidites can potentially be used as a novel P,O ligand and preliminary screening results have demonstrated their application as chiral organic catalysts.