Date of Award
Spring 5-2019
Degree Type
Honors College Thesis
Department
Chemistry and Biochemistry
First Advisor
Douglas Masterson
Advisor Department
Chemistry and Biochemistry
Abstract
The use of chiral [2.2]paracyclophane Schiff-base ligands has been shown to induce enantioselectivity in the copper catalyzed cyclopropanation of styrene with diazoesters. 1 Previous research by Dr. Masterson tested Schiff-base ligands based on 4- amino[2.2]paracyclophane with moderate enantioselectivity. In this project, the Schiff-base N- salicylidene-4-amino[2.2]paracyclophane, was modified by way of Grignard addition to the imine carbon and its enantioselective properties were explored with the copper catalyzed cyclopropanation. The methyl Grignard addition to N- salicylidene-4-amino[2.2]paracyclophane was successful in producing the amino alcohol and the amino alcohol was characterized. The amino alcohol was produced from the R enantiomer of the Schiff-base and used as an asymmetric ligand in copper catalyzed cyclopropanation of styrene with ethyl diazoacetate (EDA). Using 1H-NMR integration, a cis:trans ratio of 1:2.4 was obtained. Examination of the HPLC peaks from the asymmetric cyclopropanation confirms the existence of an enantiomeric excess (%ee) and further purification will reveal the numerical value. The existence of a cis:trans ratio and %ee proves that the amino alcohol ligand was capable of inducing enantioselectivity for both cis and trans isomers.
Copyright
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Recommended Citation
Dawoud, Yousef, "A Study on the Modifications of [2.2]paracyclophane and their Effects on the Enantioselectivity of the Copper Catalyzed Cyclopropanation Reaction" (2019). Honors Theses. 693.
https://aquila.usm.edu/honors_theses/693