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Date of Award


Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science


Biochemistry & Molecular Biol.

First Advisor

Dr. Kristine N. Nolin


Calcium(II) complexes are proving to be versatile catalysts for the activation of electron deficient cyclopropanes in addition reactions. The synthesis of γ-sulfanyl malonate was achieved through the homologous conjugate addition of thiols to electron deficient cyclopropanes. These addition reactions were catalyzed by calcium acetylacetonate, Ca(acac)2, and did not require prior activation or exogenous base. Differentially substituted γ-sulfanyl malonates were synthesized in good to excellent yield. In addition, the activation of cyclopropanes by calcium(II) complexes has been expanded to include 1,3-dipolar additions. In the presence of a calcium(II) complex, the reaction of nitrones with electron-deficient cyclopropanes provides the corresponding tetrahydro-1,2-oxazine in good to excellent yield with high diastereoselectivity.