Title

Enantioselective Organocatalyzed Hetero Diels-Alder Reactions

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Summer 2014

Abstract

The hetero Diels-Alder reaction has been investigated by using different organocatalysts. The Diels-Alder reaction has proven to be one of the most powerful reactions in organic chemistry for making six-membered carbo or heterocyclic compounds, which are used in the production of various pharmaceutical and medicinal compounds. The organocatalysts in this research project exhibit the unique feature of having an ionic liquid or an ammonium ion moiety, making them recyclable. When various aldehydes react with different enones followed by hydrolysis, the anomers which result are then oxidized by adding pyridinium chlorochromate (PCC) to give the heterocyclic ketones. From initial results, high yields and enantioselectivites were obtained by using different catalysts. In this research, various precursors for the hetero Diels-Alder reactions were synthesized, purified and characterized by different spectroscopic techniques. The reaction has been studied by using Molecular modeling to determine the nature of the transition state for these reactions.

Advisor

Allan D. Headley

Subject Categories

Chemistry | Physical Sciences and Mathematics

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