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One-Pot Synthesis Of Bicyclic Piperidines From Donor Acceptor Cyclopropanes, David G. Stephens

Electronic Thesis and Dissertation Repository

The efficient synthesis of heterocyclic compounds is of great importance to organic chemistry. One method for achieving efficiency is through the use and development of one-pot reactions. This thesis describes the planning and development of an extension to the tandem cyclopropane opening Conia-ene reactivity previously reported. A search for a substrate capable of undergoing the reaction was undertaken and the reaction was optimized. The highest yielding conditions tested used catalytic Sc(OTf)₃ and superstoichiometric ZnBr₂, but other catalyst systems also worked. The optimized reaction conditions tolerated 6-membered rings well in addition to 7-membered rings in some rotationally restricted …