Date of Degree

9-2015

Document Type

Dissertation

Degree Name

Ph.D.

Program

Chemistry

Advisor

Stacey E. Brenner-Moyer

Subject Categories

Organic Chemistry

Keywords

Organocatalysis

Abstract

The field of asymmetric catalysis embodies the efforts of chemists to mimic the stereoselectivity routinely achieved by biological systems. Asymmetric organocatalysis, a sub-field of asymmetric catalysis, is broadly based on the catalytic activity of non-transition metal, small molecules that transmit chirality to substrates. This dissertation describes experimental work towards the construction of versatile, medicinally-relevant molecular scaffolds using chiral, diarylprolinol silyl ether organocatalysts. Specifically, these catalysts were used in 1-pot, iminium-enamine catalyzed cascade reactions to functionalize α,β-unsaturated aldehydes. A comprehensive review of iminium and enamine organocatalysis is provided, including its development towards iminium-enamine cascade reactions. This review provides background for the original research recounted herein, which are 1) Accessing Medicinally-Relevant Cyclohexene Scaffolds via a Michael-Michael Organocascade, 2) One-Pot Preparation of Enantiopure Fluorinated β-Amino Acid Precursors, and 3) Accessing Medicinally-Relevant Tetrahydrofuran Scaffolds via Organocascade Reactions.

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