Semester
Spring
Date of Graduation
2023
Document Type
Thesis
Degree Type
MS
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Margaret Hilton
Committee Co-Chair
Carsten Milsmann
Committee Member
Brian Dolinar
Abstract
Dihydropyridines are a practical organic scaffold commonly used for their pharmaceutical properties. Nucleophilic dearomatization of pyridines has proven to be a useful method in obtaining dihydropyridines. By using N-heterocyclic carbene (NHC) organocatalysts, dihydropyridines can be synthesized with high regioselectivity of the 1,4 regioisomer over the 1,2- regioisomer but often with low enantioselectivity. By incorporating non-covalent interaction contact points, we hypothesize that enantioselectivity can be enhanced. By synthesizing numerous NHCs, each proposed to exhibit a different type of non-covalent interaction (i.e., hydrogen bonding or ion pairing), an understanding of the secondary interactions within this reaction system can be studied and catalysts can then be rationally designed while considering these interactions.
Recommended Citation
Patterson, Jack A., "Enantioselective Dearomatization Facilitated by Non-Covalent Interactions of N-Heterocyclic Carbene Catalysts and Pyridinium Salts" (2023). Graduate Theses, Dissertations, and Problem Reports. 11703.
https://researchrepository.wvu.edu/etd/11703