Grant: Discovery Grants Program - Individual

This proposal details plans for the development of new and useful synthetic methodologies which will be applicable to the synthetic organic chemistry diaspora. More specifically the proposal describes plans to 1) broaden the scope of the widely popular field of donor acceptor cyclopropanes, 2) develop new methods for the useful functionalization and elaboration of indoles and other heterocyclic compounds, and 3) develop new annulation strategies for the synthesis heterocyclic compounds. Our group has been involved in the field of donor-acceptor cyclopropanes for almost 25 years and was heavily involved in the resurgence of this area of organic chemistry research. In this proposal we will describe new methods of activating cyclopropanes toward ring opening and annulation. This includes hydrogen bonding activation and VilsmeierHaack activation. In addition we will describe the use of these cyclopropanes in the synthesis of dendrimers. The proposal will also include a collaborative effort with Paul Ragogna in our department which explores the hydrophosphination of donor-acceptor cyclopropanes. One of our earliest forays into the use of donor-acceptor cyclopropanes included the use of indoles as nucleophiles for the ring opening event. This spawned a new theme in our group centered around the functionalization of indoles. This application will build on this theme of indole functionalization and will include other heterocyclic compounds as well. This will include but not be limited to the tandem ring-opening/Conia-ene reactions of alkynyl-substituted heterocyclic motifs. Our group has a strong interest in the synthesis of heterocyclic compounds via both annulation and cycloaddition. We will continue to develop this area of research. This will include but not be limited to the reactions of donor-acceptor cyclopropanes. As stated, this research should provide useful methodologies which will be of great interest to the wider chemical community. The research program described in the application will also be of tremendous training value since the students performing the research will gain experience in all aspects of synthetic organic chemistry.