This project will involve the study of intermolecular radical trapping of captodative stabilized radicals. This work has important implications in two major areas: 1) the development of new intermolecular radical traps and 2) the use of chiral glycine radical templates for the asymmetric synthesis of natural and non-natural amino acids. Given the tremendous utility of radicals in organic synthesis there is a real need for the development of new intermolecular radical traps. Radical traps that will be developed include nitrones, stannyl nitronates, vinyl aziridines (for both the synthesis of allyl amines and pyrrolidines), enol stannanes, stannyl alkynes, and chiral dehydroalanines. For the asymmetric synthesis of amino acids, several chiral glycine radical templates will be investigated including a chiral diketo piperazine, oxazolidine, and 9-phenyl menthol amino acid ester. Intermolecular trapping reactions of the chiral glycine radicals will be carried out with both established radical traps (such as allyl and vinyl stannanes) and with the novel radical trapping agents. This work will be an important contribution to the areas of radical chemistry and asymmetric amino acid synthesis. %%% Research Planning Grants enable women who have not had prior independent Federal research support to develop a competitive research proposal. This project involves the trapping of stabilized free radicals, i.e., molecules with unpaired electrons, for the construction of organic molecules. Such reactions may have wide applicability in organic chemistry and complement other organic synthesis methods.
