Simultaneous Generation and Subsequent Cycloaddition of <i>ortho</i>‐Quinonemethides and Cyclic Enecarbamates Promoted by a Gold/Lewis Acid Catalytic System

Abstract

A new catalytic reaction to synthesize structurally complex hexahydrochromeno[2,3‐ b ]pyrrole derivatives from simple 3‐butynamine and 2‐(hydroxymethyl)phenol derivatives is described. The process is promoted by a dual catalytic system formed by a gold complex and a Lewis acid (boron trifluoride). The reaction involves the synchronized transformation of the starting materials into two reactive intermediates, a cyclic enamine derivative and an ortho ‐quinone methide, that subsequently react between them through a formal [4+2] cycloaddition to furnish the final poly‐heterocyclic product in a straightforward way.