Graduation Year

2024

Document Type

Campus Only Senior Thesis

Degree Name

Bachelor of Arts

Department

Biochemistry

Reader 1

Dr. Anna G. Wenzel

Reader 2

Dr. Sadie Otte

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© 2024 Jayati Anshu

Abstract

Nine out of the top ten pharmaceutical drugs possess chiral stereocenters, and investigation of molecular chirality is required when determining if a medication is safe or effective in accordance with the FDA's guidelines. In previous research, the Wenzel group found that coinage metal catalysts—gold and silver—were effective, highly selective, stable, environmentally benign, and more economically beneficial than other transition metal catalysts. These catalysts can be used to direct the formation of carbon-carbon bonds, thereby having use in the construction of pharmaceutical building blocks. This project involves the exploration of AgSbF6 for the preparation of chiral amines from benzylic alcohols via an SN1-type amination reaction. Specifically, we have been employing chiral auxiliaries of benzyloxy carbamate to control asymmetric induction, which if successful, can be applied towards the preparation chiral arylmethylamines, a structural motif common in antidepressant and beta blocker pharmaceuticals. Of the auxiliaries investigated to date, a menthol-derived carbamate has led to the best results.

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