Desymmetrization of deiesters and dinitriles to synthesize enantioenriched lactones
- UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
- Amber M. Kelley (Creator)
- Institution
- The University of North Carolina at Greensboro (UNCG )
- Web Site: http://library.uncg.edu/
- Advisor
- Kimberly Petersen
Abstract: Many significant bioactive compounds contain quaternary or fully substituted chiral centers. The stereoselective synthesis of these compounds is challenging, yet highly desired because quaternary chiral centers are an important framework in biologically active molecules. This research describes asymmetric methodologies that synthesize novel scaffolds that contain challenging chiral centers to access. Utilizing a desymmetrization reaction of diesters and dinitriles catalyzed by commercially available Brønsted acids, the synthesis of lactones that contain fully substituted chiral centers is obtained. Previous work completed in the Petersen lab involved an intramolecular desymmetrization of hydroxy-diesters by a chiral phosphoric acid to generate a series of ?-lactones. The first project describes an application of the desymmetrization reaction developed to synthesize novel spirolactones and spirolactams with good yields and stereoselectivity. The next project is the development of desymmetrizations of diesters to access diverse scaffolds of lactones such a novel 1,4-morpholinones, 1,4-dioxanones, and 3,4-dihydrocoumarin with good to excellent yields and enantioselectivities. Lastly, a unique desymmetrization of dinitriles was examined to generate lactones with multiple stereocenters including a quaternary chiral center. This research entails efficient methodologies to access important lactones scaffolds that contain challenging chiral centers.
Desymmetrization of deiesters and dinitriles to synthesize enantioenriched lactones
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Created on 8/1/2020
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Additional Information
- Publication
- Dissertation
- Language: English
- Date: 2020
- Keywords
- Chiral Bronsted Acid, Chiral Phosphoric Acid, Desymmetrization, Lactones
- Subjects
- Lactones
- Phosphoric acid
- Chirality
- Phosphodiesters