Date of Award
12-2021
Degree Type
Honors College Thesis
Academic Program
Chemistry BS
Department
Chemistry and Biochemistry
First Advisor
Douglas Masterson, Ph.D.
Second Advisor
Bernd Schroeder, Ph.D.
Third Advisor
Sabine Heinhorst, Ph.D.
Advisor Department
Chemistry and Biochemistry
Abstract
A popular method for the enantioselective synthesis of substituted malonic half esters is hydrolysis via Pig Liver Esterase (PLE), however some substrates produce low enantiomeric excess, namely benzyl-substituted malonic esters. Presented here are alternative methods explored for this synthesis, the first being phase-transfer catalyzed hydrolysis via N-benzyl quaternary ammonium salts derived from cinchona alkaloids. The second method utilized chiral auxiliary directed benzylation with auxiliaries including menthol and oxazolidinones. Though unsuccessful, this research provided valuable groundwork in the investigation for the enantioselective asymmetric synthesis of benzyl-substituted malonic acid esters.
Keywords: Pig Liver Esterase, Enantioselectivity, Phase-Transfer Catalysis, Cinchona Alkaloids, Quaternary Ammonium Salts, Chiral Auxiliary, Menthol, Oxazolidinones
Copyright
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Recommended Citation
Hansen, Madison, "Techniques for the Enantioselective Asymmetric Synthesis of Benzyl Substituted Malonic Acid Esters" (2021). Honors Theses. 866.
https://aquila.usm.edu/honors_theses/866