Development and synthesis of chiral dirhodium carboxylate catalysts and their applications in asymmetric carbenoid and nitrenoid transformations
Reddy, Ravisekhara P.
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Chiral catalysts play an important role in the advancement of synthetic organic chemistry. The Davies group is interested in the development of chiral dirhodium catalysts and their utilization in donor/acceptor diazo decomposition reactions. Rh 2 ( S -DOSP) 4 catalyzed intermolecular carbenoid transformations lead to diverse products with excellent selectivity. The first chapter of this thesis explores the limitations of the currently available dirhodium catalysts and the design and synthesis of novel phthalamide-based dirhodium catalysts. Applications of these new catalysts in various carbenoid reactions are discussed. The second chapter focuses on the development of an asymmetric methodology for the synthesis of tropanes by rhodium-catalyzed [4+3] cycloaddition. This methodology has been extended to a range of electronically and structurally diverse pyrroles and furans. This asymmetric tandem cyclopropanation Cope rearrangement was then successfully applied in a key step of the enantioselective synthesis of (-)-isostemofoline. The third chapter describes the development of asymmetric amination methodology using chiral dirhodium catalysts and their applications in both intramolecular as well as intermolecular amination reactions.