Indium triflate-catalyzed stereoselective tandem intramolecular conjugate addition of secondary amines to α,β-bisenones

Abstract

We report an indium triflate-catalyzed stereoselective intramolecular tandem conjugate addition of secondary amines to α,β-bisenones to afford a 1,2,3-trisubstituted six-membered ring bearing diketone substituents in good to excellent yields at room temperature. Various kinds of α,β-bisenones and amines were employed to expand the scope of this chemistry. Intramolecular trapping of indium-enolate by the tethered electrophiles resulted in the stereoselective formation of three contiguous stereogenic centers.