Dihydropyrans are highly attractive targets in chemical synthesis based on their prevalence in numerous biologically active natural products. This poster describes the development of a method for obtaining dihydropyrans using Re2O7 catalyzed dehydrative cyclization of 1,3-diols, in which one of the alcohols serves as a precursor to allyl cation formation. These reactions proceed to give the dihydropyrans that afford the 2,6-trans isomer as the major product. We initiated a mechanistic investigation through manipulating functional groups and olefin geometry. A solvent screen was done to determine the optimal system for yield and stereocontrol. A substrate scope was investigated to determine the functional group tolerance, effects of pendant stereocenters and application to synthesizing enantiopure monosubstituted dihydropyrans successfully.

Re2O7 -mediated dehydrative cyclizations: Method towards 2,6-trans dihydropyran synthesis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.