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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Biochemistry & Molecular Biol.
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.
Braun, Caroline M., "Addition reactions of electron-deficient cyclopropanes catalyzed by calcium(II) complexes" (2014). Honors Theses. 890.