One-pot synthesis of new highly substituted allylic phosphorodiamidates

•Nine new allylic phosphordiamidates were synthesized using a one-pot reaction pathway.•The results clearly show the effect of the CF3 group on the reactivity of the starting alcohols.•The in situ phosphorylation products were more favored with fluorinated alcohols compared to non fluorinated ones.

A one-pot synthesis of new substituted allylic phosphorodiamidates was performed through phosphorylation of the corresponding alcohols followed by aminolysis. The intermediate allylic phosphorodichoridates could only be isolated when the starting allylic alcohol contains a trifluoromethyl group at the γ-position. These phosphorodiamidates were obtained as mixtures of two (Z and E) isomers in 41–72% yield. They were characterized by multinuclear (1H, 13C, 31P and 19F) NMR, IR spectroscopy and HRMS.

Graphical abstractNew allylic phosphorodiamidates were prepared using a one-pot synthesis through phosphorylation of the corresponding alcohols followed by aminolysis. The intermediate allylic phosphorodichoridates could only be isolated when the starting allylic alcohol contains a trifluoromethyl group at the γ-position.Figure optionsDownload full-size imageDownload as PowerPoint slide