Lewis Base-Catalyzed [4 + 3] Annulation of <i>ortho</i>-Quinone Methides and MBH Carbonates: Synthesis of Functionalized Benzo[<i>b</i>]oxepines Bearing Oxindole Scaffolds

Abstract

A novel Lewis base-catalyzed [4 + 3] annulation process for the construction of benzo[ b]oxepine scaffolds has been developed. 1,4-Diazabicyclo[2.2.2]octane (DABCO) promotes the union of o-QMs and Morita-Baylis-Hillman carbonates in reasonable to excellent yields and good stereoselectivities (dr > 20:1). This straightforward, catalytic approach offers access to a variety of synthetically useful benzo[ b]oxepine derivatives bearing oxindole scaffolds containing all-carbon spiro-quaternary stereocenters.