Date of Award


Degree Type

Honors College Thesis

Academic Program

Chemistry BS


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


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