Direct Construction of 2,3-Dihydroxy-2,3-diaryltetrahydrofurans via N-Heterocyclic Carbene/Base-Mediated Domino Reactions of Aromatic Aldehydes and Vinyl Selenone.

A one-pot, stereoselective construction of 2,3-dihydroxy-2,3-diaryltetrahydrofurans has been achieved via N-heterocyclic carbene (NHC)/base-mediated domino reactions of aldehydes and vinyl selenone. The products containing two contiguous quaternary hydroxyl functionalities among the three stereocenters are obtained advantageously as either acetals or ketals through the formation of five new chemical bonds in a single operation. This report constitutes an altogether different reactivity of vinyl selenone in comparison with the corresponding sulfones and phosphonates under NHC/base-mediated reactions.