Allylic hydroxy phosphonates: versatile chiral building blocks

Allylic hydroxy phosphonates are converted into beta and gamma 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 gamma-substituted phosphonates, whereas, reaction of tosyl carbamates with palladium (II) and base gives oxazolidinones (beta-substitution). (c) 2004 Elsevier B.V. All rights reserved.