Reports: UR155707-UR1: Organocatalytic Domino Reactions for the Synthesis of Highly Substituted Heterocycles
Shanina Sanders Johnson, PhD, Spelman College
Current efforts within the group are focused on the synthesis of acyclic Baylis-Hillman adducts that will couple with imines and nitrones to form cyclic piperidines and oxazepines respectively. Progress has been made in accessing Morita Baylis- Hillman (MBH) adducts with varying electronic profiles. MBH reactions of methyl vinyl ketone and several acrylates have provided these compounds with the acrylates generating better yields of the products. These syntheses have proven to be challenging, but some novel compounds have been created and are currently being characterized. Protocols for these syntheses are being optimized in terms of selectivity since geometric isomers are present with some derivatives and are difficult to isolate. Efforts have also been made to perform this reaction in the microwave synthesizer to reduce reaction times. One other variable that is being accessed is the diester group. This group is responsible for the strength of the base that is needed in the cyclization and currently only strong bases show any reactivity. Going forward this functional group will be optimized to allow for milder bases in the cyclization. Overall, the optimizations to the structure of the MBH adduct are expected to afford the cyclization products in a controlled and efficient manner.
Impact of Grant
Student Research- The synthetic research that has been performed thus far has impacted the research environment for students and allowed the PI to sustain an active research group. Funding from PRF has increased the PI’s ability to recruit students into research positions and offer financial support for students to work on campus in a research capacity. The PI has mentored six undergraduate research students, four during the academic year and two during the summer, with support from this grant. All were Black women. Two are graduates of Spelman College and one of those graduates recently defended her Masters thesis in a chemistry program.
The independent research projects taken on by students allow them to learn a variety of basic organic reactions and techniques while synthesizing the desired products. Students are also able to use advanced instrumentation such as nuclear magnetic resonance (NMR)spectroscopy in the course of their research. These skills serve to make the students more competitive for internships, jobs, and admission to graduate and professional schools. All students who participate in research present at Spelman’s annual Research Day in the Spring semester and students have also presented at other local conferences. Plans are in progress for the recent summer students to present at a national conference. In addition to supporting a productive work environment with undergraduate students, this award has also allowed the PI to participate in scholarship via funds for summer salary and research supplies. The research lab is active year-round which allows for a consistent flow of ideas and scholarly work. This is not only stimulating for the research group, but also for the Department of Chemistry and Biochemistry at Spelman College. The department has a more diverse portfolio of research and more research opportunities to provide for students. The PI recently traveled to the Fall meeting of the American Chemical Society with travel funds provided by the award. The networking and academic environment at the conference provided some new insight into the current project and presentations related to this project are expected at future conferences.