A novel application of organocatalysis for the synthesis of six-membered ring lactones

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Tylisha M. Baber (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/
Kimberly Petersen

Abstract: Brønsted acid catalysis is an emerging area of organocatalysis. The small and labile nature of an acidic hydrogen atom and its interaction with substrates containing basic functional groups allows for the preparation of diverse compounds. When the substrate consists of an electrophile and nucleophile in its structural make-up, the bifunctional nature of a Brønsted acid is an attractive synthetic feature for intramolecular cyclization reactions to form heterocycles. Heterocycles are cyclic compounds containing at least one non-carbon atom, typically oxygen, nitrogen, or sulfur; and are ubiquitous frameworks in both naturally occurring and pharmaceutical compounds that are bioactive. Lactones are cyclic esters derived from aliphatic hydroxy acids and are a key structural framework in many natural products that exhibit a wide range of biological activity, with five- and six-membered ring lactones being the most common. Novel synthetic approaches for their preparation are necessary to readily access these compounds. The work described in this thesis provides a novel application of organocatalysis for the synthesis of six-membered ring lactones. The synthesis is carried out by activating hydroxynitriles via a bifunctional Brønsted acid to drive an intramolecular cyclization reaction, generating the desired functionalized lactones. This project contributes to the research scope of utilizing nitriles as versatile building blocks in organic synthesis.

Additional Information

Language: English
Date: 2019
Brønsted acid, Lactone, Nitrile, Organocatalysis
Organic compounds
Heterocyclic compounds

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