Facile synthesis of enantioenriched hydroxy esters via Brønsted acid catalyzed kinetic resolution

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

Abstract: The synthesis of natural products is a growing area of research within the field of chemistry. Compounds are extracted from sources such as fungi, plants, algae, and other natural sources. The compounds that are biologically active often need to be synthesized in the laboratory due to the fact that the natural resources only contain scant amounts of the active compound. In this research, kinetic resolution, a form of asymmetric synthesis, is used in conjunction with Brønsted acid catalysts to form enantioenriched small molecules that can later be used in the synthesis of natural products. The Petersen lab chose to focus on substituted ?-hydroxy tert-butyl esters. The small molecule was lactonized via a Brønsted acid catalyzed kinetic resolution yielding enantioenriched starting material. In kinetic resolution, the maximum amount of material that can be achieved is 50% with an enantiomeric excess of 100%. Initial optimization was conducted on a-substituted ?-hydroxy tert-butyl esters which showed that R-TRIP was the best catalyst in the kinetic resolution. ?-Substituted and disubstituted ?-hydroxy tert-butyl esters were tested with the syn-a,?-dimethyl substrate showing the highest selectivity (s = 15.6). Cyclic hydroxy esters are currently being tested.

Additional Information

Language: English
Date: 2014
Enantioenriched, Hydroxy ester, Kinetic resolution, Lactone, Natural product synthesis, Synthesis
Asymmetric synthesis
Natural products $x Synthesis

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