Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates.Org Lett. 2008 Jun 19; 10(12):2425-8.OL
The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism. On the other hand, under palladium-catalyzed conditions, the reaction shows a strong solvent-dependent regiocontrol, affording exclusively one of the two possible regioisomers with complete transfer of chirality from the substrates to the products.