Pyridyl and acetylenic bicyclobutanes have medicinal potential either as bioisosteres themselves or in the strain-release synthesis of cyclobutanes. Our objective is to synthesize these systems by gamma silyl elimination/bridging of precursor cyclobutyl systems with appropriate leaving groups. Previous attempts to bridge these systems under solvolytic conditions with polar protic 2,2,2-trifluoroethanol (TFE) under solvolysis conditions or with aprotic THF using fluoride ion resulted in formation of minor to no amounts of product.  We have been exploring different leaving groups as well as using a variety of anionic initiators to achieve bridging by assisting with removal of the silyl group.<br/>

Trifluoroethoxide assisted formation of electron-withdrawing substituted bicylobutanes

2019 Spring National Meeting

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