Diastereoselective Synthesis of Pyranoquinolines on Zirconium‐Containing UiO‐66 Metal‐Organic Frameworks

Abstract

The Zr terephthalate MOFs UiO‐66 and UiO‐66‐NH2 have been found to be highly diastereoselective catalysts for the synthesis of a pyrano[3,2‐c]quinoline through an inverse electron‐demand aza‐Diels–Alder [4+2] cycloaddition of an aryl imine (formed in situ from aniline and benzaldehyde) and 3,4‐dihydro‐2H‐pyran in one pot, affording the corresponding trans isomer in diastereomeric excesses of 90–95 %. The solids are stable under the reaction conditions and can be reused at least three times without significant loss of activity or diastereoselectivity.