Recyclable tetraarylphosphonium supported chiral imidazolidin-4-one organocatalyst for Diels–Alder reactions

The tetraarylphosphonium supported chiral imidazolidin-4-ones were synthesized and used to catalyze the Diels–Alder reactions of cyclopentadiene and α,β-unsaturated aldehydes. High enantiomeric excesses and good yields were obtained, and catalyst recycling (up to five cycles) was accompanied by almost intact enantioselectivity and some loss of the chemical efficiency.

► The tetraarylphosphonium supported chiral imidazolidin-4-ones were synthesized. ► The supported catalysts were used to catalyze the Diels–Alder reactions. ► High enantiomeric excesses and good yields were obtained. ► Catalyst was recycled several times without loss of its activity.