Asymmetric synthesis of enantioenriched spirocycles via a chiral Brønsted acid catalyzed desymmetrization

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Eni Minerali (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site:
Kimberly Petersen

Abstract: Asymmetric methodologies are very important as they allow chemists to produce significant quantities of complex chiral molecules as enantiopure or enantioenriched compounds. The Petersen group has previously developed chiral Brønsted acid catalyzed desymmetrization reactions for the asymmetric synthesis of lactones. The work described in this thesis provides an application for this methodology to the synthesis of enantioenriched spirocycles, motifs present in many biologically active molecules. This synthesis is performed in the presence of TRIP, a chiral BINOL-derived phosphoric acid catalyst, which guides the cyclization of symmetric prochiral intermediates. The research in this thesis describes the synthesis of two enantioenriched spirocycles, one of which posed many synthetic challenges. Even though the results were nonconclusive, more synthetic work towards the understanding of the mechanistic pathway is also introduced. Therefore, the work described herein not only contributes to the substrate scope of the reaction that was developed, but also provides discussion to the challenges faced during the synthesis of these compounds.

Additional Information

Language: English
Date: 2019
Asymmetric, Catalysis, Chiral, Desymmetrization, Organic synthesis, Spirocycles
Asymmetric synthesis

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