Allylic hydroxy phosphonates: versatile chiral building blocks

Allylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).

Graphical abstractAllylic hydroxy phosphonates are converted into β and γ substituted amino phosphonates using a series of palladium-catalyzed reactions. The judicious selection of nitrogen nucleophile and palladium catalyst allow for excellent regio- and stereochemical control. Palladium(0)-catalyzed amine addition or tosyl carbamate rearrangement gives rise to the γ-substituted phosphonates, whereas, reaction of the tosyl carbamates with palladium (II) and base gives oxazolidinones (β-substitution).Figure optionsDownload full-size imageDownload as PowerPoint slide