Construction of Carbo- and Heterocycles Through Alkene Difunctionalization
Restricted (Penn State Only)
- Author:
- Lakomy, Margaret
- Graduate Program:
- Chemistry
- Degree:
- Doctor of Philosophy
- Document Type:
- Dissertation
- Date of Defense:
- June 10, 2024
- Committee Members:
- Benjamin Lear, Major Field Member
Ramesh Giri, Chair & Dissertation Advisor
Eric Nacsa, Major Field Member
Kenneth Luther Knappenberger, Jr., Program Head/Chair
Emily Weinert, Outside Unit & Field Member - Keywords:
- Catalysis
cyclization
heterocycles - Abstract:
- The development of rapid and concise synthetic methods is highly desirable for application in total synthesis. A key route for achieving this has been the difunctionalization of alkene compounds through transition metal catalysis or visible light mediation. Both methods rely on the incorporation of two new groups across the alkene in a single step resulting in rapid increases in molecular complexity. The synthesis of carbo- and heterocycles through these methods has received great interest due to those scaffolds presence across natural products as well as the potential for further reactivity. The development of these synthetic routes has presented challenges concerning the controlled ring formation with hetero atoms, the presence of unwanted side reactions, and with utilization of mild conditions through simple reactants. This dissertation outlines two approaches for cyclization of alkenes to access carbo- and heterocycles through transition metal catalysis and visible light mediation. The first will demonstrate the synthesis of oxasilolanes and the further products that can be accessed by linearizing the scaffold. The second will demonstrate visible light initiated cyclization to form 2,3-dihydrofurans as well as cyclopropanes. In summary, these reactions introduce new methods for the difunctionalization of alkenes to reach of carbo- and heterocycles.