The long-term objective of the research described in this proposal is the development of Pt- and Au- catalyzed protocols for the intramolecular hydrofunctionalization of unactivated alkenes and allenes with carbon, nitrogen, and oxygen nucleophiles that display the generality, efficiency and selectivity (chemo-, regio-, and stereo-) required for application to the synthesis of biologically relevant heterocyclic compounds in both academic and pharmaceutical environments.
Our specific aims for the tenure of this proposal are to 1) optimize and expand the scope of the platinum-catalyzed intramolecular hydroamination of alkenyl amines and the gold-catalyzed hydroamination of N-alkenyl and N-allenyl carboxamide derivatives, 2) apply Pt- and Au-catalyzed hydroamination to the synthesis of bicyclic nitrogen compounds, cyclic carboxamide derivatives, and the alkaloids (+)-241D, (-)-Sedamine, and (-)-Allosedamine, 3) identify an effective catalyst system for the asymmetric hydroamination of allenes, 4) investigate the scope of the Au-catalyzed intramolecular hydroarylation of chiral allenyl alcohols, 5) optimize and expand the scope of the Au- catalyzed intramolecular asymmetric hydroalkoxylation of allenes, 6) apply catalytic asymmetric hydroalkoxylation to the desymmetrization of prochiral allenyl alcohols and to the synthesis of d-Nebivolol, 7) optimize and expand the scope of the catalytic hydroarylation of alkenes and allenes with electron-rich arenes and to apply catalytic hydroarylation to the synthesis of Milnamide C, 8) optimize and expand the scope of the intramolecular asymmetric hydroarylation of unactivated alkenes and allenes with electron-rich arenes. Drug design and pharmaceutical development rely on general, reliable, and selective methods for the generation of a diverse range of molecular sub-structures. For this reason, the development of new and efficient methods for the construction of a variety of molecular structures is of central importance in organic synthesis. The activities described in this proposal will lead to the development of new synthetic methods that will facilitate the development of new drug targets and pharmaceuticals. ? ? ?
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