Novel olefin additions and carbon-carbon bond forming reactions
Timmons, James C.
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As the nation's population and life expectancy continue to increase, the development of new molecules of biological and medicinal importance has moved to the forefront of modern science. Central to this theme is the development of new synthetic strategies for the construction of these molecules. In particular, the transformation of simple, readily available starting materials into highly functionalized synthetic intermediates is among the most important challenges facing the organic chemist today. In this dissertation, several new methodologies are reported for the synthesis of novel amines, alcohols, ethers, and related compounds. The first class of reactions deals with the oxidation of olefins to afford vicinal diamines. Such compounds are of great importance due to their similarity to amino acids. However, with the presence of an additional amine group, these compounds can significantly complement natural amino acids in a variety of roles. In particular, peptide studies and catalysis research can greatly benefit from the ready availability of vicinal diamnes. The second class of reactions reported herein involves the construction of new carbon-carbon bonds. Halo aldol, Mannich, and Morita-Baylis-Hillman reactions are reported that are significantly more functionalized than their non-halogenated counterparts, thus making them more useful building blocks. The majority of these reactions were rendered asymmetric. In addition, the work has been extended to include the preparation of 5- and 6-membered oxygen and nitrogen heterocycles.