Vinyl selenones derived from D-fructose: a new platform for fructochemistry

Abstract

D-Fructose, an inexpensive biomass precursor available on a large scale, has been used for the generation of enantiomerically pure chemical entities. Construction of vinyl selenone moieties on cyclic skeletons of d-fructose led to the highly reactive synthetic intermediates comprising of an electron-deficient double bond along with an excellent leaving group. Reactions of these Michael acceptors with different nucleophiles afforded aziridines, thiiranes, cyclopropanes, dihydrofurans, dihydroisoxazole, dibenzyloxymethylfuran, and isonucleosides in moderate to good yields. This powerful and practical route provides a new platform for synthetic applications of renewable biomass precursors and adds to the toolbox for chemists interested in new chemical entities.