Palladium catalysed sythesis of stereodefined alkenyl boronate esters

Undergraduates: Eugenia Luc, Stephanie Murray Michael Liang

Faculty Advisor: Simon Meek
Department: Chemistry

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Methods of making stereodefined secondary alcohols are important in the synthesis of biologically relevant compounds. This project explores the formation of such an alcohol adjacent to a vinyl boronate ester from the deprotonation of diborylmethane and subsequent reaction with a stereodefined epoxide in the presence of a palladium catalyst. The products are afforded in good yield and high E:Z selectivity (>20:1). HPLC traces using pure and racemic starting material provide evidence of the mechanism proceeding without the erosion of enantioselectivity. The substrate scope explored a range of readily available aryl epoxides. This approach allows for further functionalization due to the versatility of boron in transformations into more useful products.