Highly asymmetric synthesis of (+)-corsifuran A. Elucidation of the electronic requirements in the Ruthenium-NHC catalyzed hydrogenation of benzofurans

Article abstract of DOI:10.1016/j.tet.2012.03.109

A short and efficient synthesis of ent-corsifuran A by a highly asymmetric hydrogenation of a benzofuran precursor is reported. In addition, the electronic influence of the substituents on the asymmetric hydrogenation of benzofurans is provided. Whereas the hydrogenation of electron-deficient benzofurans was achieved under very mild conditions, the presence of electron-donating groups in the benzofuran required harsher reaction conditions for achieving full conversion to the 2,3-dihydrobenzofuran.