Acyclic ketene aminal phosphates derived from N,N-diprotected acetamides: stability and cross-couplings

The synthesis of a stable ketene aminal phosphate (alpha-phosphoryloxy enecarbamate) derived from N,N-diprotected acetamide, bearing two different removable protecting groups, is disclosed. This synthetic intermediate underwent Successful palladium-catalyzed cross-coupling reactions to afford functionalized enynes and dienes. (C) 2009 Elsevier Ltd. All rights reserved.