Stereocontrolled intermolecular radical additions to methylidenepiperazine-2,5-diones

The use of latent amino acid functionalities for the syntheses of methylide nepiperazine-2,5-diones is reported. These piperazinediones are potential c hiral templates in the synthesis of functionalised piperazinediones and ami no acids. Carbon-carbon bond formation utilising radical addition reactions between the methylidenepiperazinediones and a number of alkyl radicals res ulted in good yields of the addition adduct. Moderate to high diastereosele ctivities were observed and factors controlling the chiral induction are di scussed here.