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  • Thesis

  • Authors: Calad, Stacie Anne (2006)

  • Silylene transfer products can undergo stereoselective carbon-carbon bond-forming reactions, including the generation of quaternary carbon stereocenters, which demonstrate their utility in synthetic organic chemistry. Our laboratory has developed a metal-catalyzed method for di-tert-butylsilylene transfer to an alkene, providing silacyclopropane products. This dissertation describes the application of the metal-catalyzed silylene transfer conditions to carbonyl compounds. Metal-catalyzed silylene transfer to a range of a,13-unsaturated esters proved to be a general method for the formation of oxasilacyclopentene products containing a cyclic silyl ketene acetal functionality. These oxasilacyclopentenes are useful synthetic intermediates that can undergo facile and selective aldol add...