This CAREER award supports the research group of Professor Gregory W. O'Neil of the Department of Chemistry at Western Washington University to explore the use of beta-acyloxysulfones as a general alkene protecting-group strategy, with an emphasis on its use in olefin metathesis to prepare important polyene compounds unobtainable by standard metathesis technology. Early work will investigate an acyloxysulfone metathesis/elimination sequence as a versatile and stereoselective approach for the construction of synthetically challenging polyene and carbocyclic targets. Additional expected insights include a detailed mechanistic understanding of samarium-mediated acyloxysulfone elimination and further data toward a general predictive olefin metathesis model. Examples of targets that can be readily prepared using the proposed strategy include a class of algal lipids known as polyunsaturated long-chain alkenones (PULCAs). A series of these compounds are to be synthesized and explored for the advancement of algal biodiesel technology.
Much of this work is to be conducted by undergraduate students, providing these students with valuable training in modern synthetic organic techniques. This research is closely integrated with an educational plan aimed at leveraging broad student interest in renewable energy to increase student participation in chemistry and related STEM fields. This is to be accomplished in part through the creation of a cross-discipline cooperative biodiesel experiment involving students at both the high school and college level in collaboration with local renewable energy industries. Specific results from the proposed research will also be incorporated into a "Biofuels" course developed by the PI and a proposed capstone "Chemistry of Energy" course. These courses are to be part of a new cross-college Clean Energy curriculum at Western Washington University.
