COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural & alpha;-Quaternary Stereogenic Glutamic Acid Derivatives

A palladium-catalyzed regioselective and asymmetric allylicalkylationof azlactones with MBH carbonates has been developed with chiral oxalamide-phosphineligands. The corresponding reaction afforded a range of opticallyactive & gamma;-arylidenyl glutamic acid derivatives bearing an & alpha;-chiralquaternary stereocenter in good yields with excellent linear regio-and high enantioselectivity. This protocol furnishes an alternativeapproach for the construction of enantio-enriched unnatural & alpha;-aminoacid derivatives.

Automated summary

A palladium-catalyzed regioselective and asymmetric allylic alkylation reaction using chiral oxalamide-phosphine ligands has been developed for the synthesis of optically active γ-arylidenyl glutamic acid derivatives. The reaction gives good yields with excellent regio- and enantioselectivity, and provides an alternative approach for the preparation of enantio-enriched unnatural α-amino acid derivatives.