Development of Methods Towards the Synthesis and Functionalization of Heteroatom-substituted Cyclopropanes

Abstract: This thesis focuses on the development of new synthetic methods for the synthesis and functionalization of heteroatom-substituted cyclopropanes, including cyclopropanols, cyclopropylamines, and cyclopropanethiols. These motifs are of significant interest due to their unique reactivity and prevalence in biologically active compounds; accordingly, the development of new strategies to overcome synthetic challenges associated with their preparation remains an important objective in synthetic organic chemistry. To address these limitations, several complementary strategies were developed. A photocatalyzed O- to S-alkyl rearrangement enables access to tertiary cyclopropanethiols from readily available cyclopropanols. A nickel-catalyzed reductive 1,2-alkylarylation of alkenes provides a modular route to 1-alkylcyclopropylamines, which can be further transformed into pharmaceutically relevant spirocyclic γ-lactams. Finally, a strategy to override traditional Norrish–Yang reactivity enables the photocyclization of β-boryl ketones to cyclopropanols via a 1,4-boryl group transfer pathway, with reactivity governed by triplet-state population control. Together, these methods provide efficient, mild, and versatile approaches to access and elaborate valuable cyclopropane scaffolds, expanding the synthetic toolbox for strained-ring chemistry and enabling new opportunities in medicinal chemistry.

Zoom Link: https://utoronto.zoom.us/j/86718537741?pwd=z1bchaB6VbVIp7o1beZao44j6a3a6s.1
Meeting ID: 867 1853 7741
Passcode: FOESeminar

This seminar will be followed by a closed oral examination.