Iridium-Catalyzed Intermolecular Enantioselective Allylic Amidation

Significance

As a follow-up to their report on intramolecular iridium-catalyzed allylic amidation (O. V. Singh, H. Han J. Am. Chem. Soc. 2007, 129, 774), the authors describe an intermolecular version. Using an Ir(I) catalyst, a chiral phosphor­amidite ligand and DBU, a variety of imidodicarb­oxylates undergo allylic amidation with ethyl allyl carbonates in high regio- and enantioselectivities. Protocols for selective deprotections of the N-groups on the imidodicarboxylates are provided, as well as conversion of the products into useful compounds such as amino acids.