Investigation into the mechanism of catalysis for the kinetic resolution of a,a-Disubstituted y-Hydroxy Esters

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

Abstract: The synthesis of enantioenriched, biologically active compounds is a vital area of interest for synthetic chemists. The lactone motif is found in several biologically important molecules, and the development of kinetic resolutions capable of producing enantioenriched lactones is important for the total synthesis of these types of compounds. The chiral Brønsted-acid catalyst, R-TRIP, has proven to be effective in producing enantioenriched a,a-disubstituted lactones with up to 94% ee. A study of the effects of varying electronic substituents on the kinetic resolution of a,a-disubstituted-?-hydroxy esters to produce enantioenriched ?-lactones is the focus of this study. The introduction of varying electron-withdrawing and electron-donating substituents in the para position of an a-Ph group is hypothesized to cause a change in the selectivity and rate of reaction through resonance, induction, hydrogen bonding and pi-stacking. This project seeks to broaden the scope and understanding of the catalyst-substrate interaction to improve upon this synthetic methodology. [This abstract has been edited to remove characters that will not display in this system. Please see the PDF for the full abstract.]

Additional Information

Language: English
Date: 2018
Enantioselective, Esterification, Kinetic Resolution, Lactonization
Esters $x Synthesis
Esters $x Synthesis

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