Structural Diversity Based on Cyclopropane Scaffolds

University Of Notre Dame, Notre Dame IN

Investigators

Abstract

Professor Taylor's group has successfully used molecules containing homoallylic alcohol and allylsilane functional groups to prepare enantiomerically pure cyclopropanes and oligocyclopropanes. In the current award period, they will study the mechanisms of these cyclopropane forming reactions and use that understanding to control future reactivity and selectivity studies. In the current project period, this group will be extending their cyclopropane forming methodology to the use of silyl enol ethers as cation traps in addition to the allyl silane traps used previously. This change will provide access to cyclopropyl aldehydes which can be further functionalized. Vinyl cyclopropyl alcohols will also be prepared and elaborated into oxepene core structures found in marine natural products. Lastly, vinyl cyclopropanes will be studied as substrates for olefin cross metathesis. This methodology will be used to prepare oligocyclopropanes and cyclopropane containing fatty acids. The fatty acids can be used to study membrane and monolayer stabilities. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Richard E. Taylor of the Department of Chemistry at the University of Notre Dame. Dr. Taylor will work on the development of chemical reactions which can be used to prepare organic molecules containing a cyclopropane ring. Cyclopropanes are three membered rings containing three carbon atoms. This functional group is found in a number of molecules with pharmaceutical and agrochemical uses. The cyclopropane ring forming reactions developed by Professor Taylor and his research group produce cyclopropanes which are chiral (have two nonsuperimposable mirror images) and make only one of the two possible forms (a single enantiomer). Development of this family of reactions is one of the most important problems facing the pharmaceutical and agrochemicals industries today. Students trained during the course of this work will gain skills needed by the pharmaceutical and speciality chemicals industries which now produce a number of single enantiomer compounds.