Researcher ORCID Identifier

https://orcid.org/0009-0007-9273-2442

Graduation Year

2026

Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Arts

Department

Biology

Second Department

Chemistry

Reader 1

Anna Wenzel

Reader 2

Aaron Leconte

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Terms of Use for work posted in Scholarship@Claremont.

Rights Information

2025 Hannah M Cohen

Abstract

Asymmetric catalysts can facilitate a reaction pathway for performing a chiral aza-Baylis-Hillman reaction, a catalyzed carbon-carbon bond-forming reaction between an electron-deficient alkene (such as an α,β-unsaturated carbonyl compound) and an imine. We hypothesized that N-methylpyrrolidine and its derivatives could function as green catalysts for this reaction due to their strong nucleophilic behavior and nontoxic properties. As a test reaction, ethyl-2,3-butadienoate and N-benzylidine-4-methylbenzenesulfonamide cleanly reacted in the presence of N-methylpyrrolidine (10 mol%) at ambient temperature with 71% conversion to product after 24 hours, affording ethyl 2-phenyl-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate, a promising GGTase inhibitor. Additional substrates have been investigated, many of which exhibit promising biological activity by behaving as anticancer and antimalarial therapeutics. The use of chiral pyrrolidines for asymmetric induction was also examined, and it was found that an ethyl-methyl-ether substituent did not provide enough steric inhibition to prevent a racemic mixture of the lead discovery product from forming. Future directions for this project include examining alternative N-methylpyrrolidine derivatives that may improve reaction stereoselectivity, including (S)-1-cinnamyl-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine and benzyl cinnamyl-L-prolinate, which will ensure safe, cheap, and expedient production of usable medicinal compounds.

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