This project will continue work on the development of methods for the formation of C-C bonds using organozinc reagents, as the formation of C-C bonds is of fundamental importance in organic synthesis. New and efficient methods will be studied for the direct conversion of aldehydes into enals, which are among the most important starting materials for organocatalytic reactions. Methods for the stereospecific synthesis of enantioenriched enamines will also be explored. Finally, new classes of enantioenriched cyclopropanes will be prepared through novel halocyclopropanations.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Patrick J. Walsh of the Department of Chemistry at the University of Pennsylvania. Professor Walsh's research efforts involve the development of novel and practical methods for the formation of C-C bonds. Such chemistry will allow multiple reactions to be performed without isolation or purification of intermediates, thus reducing the environmental impact of chemical synthesis. Successful development of these methods will positively impact organic synthesis in the pharmaceutical and agricultural industries.
Intellectual Merit: The intellectual merit of the science performed during this grant period addressed long-standing deficiencies in organic chemistry and will enable the synthesis of materials previously difficult or impossible to prepare by other methods. Two methods involve the formation of carbon-carbon bonds were developed. Carbon-carbon bonds make up the skeleton of organic compounds, such as those found in Nature and those made in the laboratory. Examples of organic compounds include: vitamins, medications, perfumes, and food additives. The methods developed during the grant period could be used to make compounds from these broad classes of organic materials. Broader Impact: The broader impact of the science performed in the grant period is that it presents new and more efficient methods to prepare valuable organic compounds. The methods are designed to be practical and scalable and could be employed in the synthesis of medications and new materials. During the proposed investigations, undergraduate and graduate researchers were trained in the art of chemical synthesis and catalysis. This training includes daily research discussions between students and the PI (the professor) as part of their education and to streamline their research. Students also participate in regular meetings to analyze articles and present research findings. The students and PI have published their results in high quality, peer reviewed journals dedicated to chemistry. Researchers at other institutions and in companies can read these publications and apply the methods that were developed during the grant period top their own research. Outside UPenn, the PI is involved in community science education of children in pre-K classes. These presentations focus on the states of matter and are designed to pique the interest of children before they are discouraged from considering studies in science. The PI has also given lectures in high school chemistry courses on the research performed in his laboratory. The PI has an outreach program designed to address deficiencies in Mexican chemical education and research. Since 1996 the PI has been committed to raising the level of chemical education in Mexico. Ongoing efforts include teaching and collaborating with Mexican scientists. This effort has produced 20 coauthored articles with 9 professors at 6 different institutions in Mexico and continued through this grant cycle.
