Heterocyclic Chemistry of Bicyclo[1.1.0]butanes

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This project will focus on the exploratory chemistry of a strained organic ring system, the bicyclobutane group. Steric strain has always been one of the major driving forces for C-C and C-heteroatom bond formations, but in contrast to cyclopropanes, oxiranes, and aziridines, only minimal progress has been made in the past in the application of the bicyclo[1.1.0]butane building block in organic synthesis. Fundamentally, bicyclobutanes represent 4-carbon alkyne surrogates. Studies to harness their intramolecular pericyclic processes will take advantage of the attachment of suitable alkenes and alkynes to a nitrogen tether and provide access to novel polycyclic pyrrolidines. Additionally, hypothesis driven transition metal catalyzed transformations will be carried out to identify new reactions and construct useful new heterocyclic scaffolds.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Peter Wipf of the Department of Chemistry at the University of Pittsburgh. Professor Wipf's research efforts revolve around the total synthesis of natural products, organometallic and heterocyclic processes, and combinatorial, medicinal and computational chemistry. The study of chemical reactivity and the use of synthesis to augment the chemical toolbox assists the development of new therapeutic strategies. The discovery of fundamentally new reaction pathways in his laboratory is stimulated by exploratory studies of transition metal complexes. Successful development of the methodology will have an impact on discovery and process chemistry in the pharmaceutical, agricultural and fine chemical industries.