Recyclable and reusable chiral α, α-L-diaryl prolinol heterogeneous catalyst grafting to UiO-67 for enantioselective hydration/aldol/oxa-Diels Alder domino reaction

Abstract

α,α-L-Diaryl prolinol was first introduced into a highly stable porous MOF, UiO-67, via the immobilization of a chiral prolinol side chain into 4,4′-biphenyldicarboxylic acid through a five-step process, to construct a chiral heterogeneous catalyst. The catalyst exhibited high yield (up to 88%) and excellent stereoselectivities (up to >4:1 dr, > 80% ee) for the enantioselective hydration/aldol/oxa-Diels Alder domino reactions, as well as good reusability with recycle use for three times without significant loss of activity. To our knowledge, this is the first report of chiral MOFs as heterogeneous catalysts for asymmetric domino reactions.

Keywords

• α,α-L-Diaryl prolinol
• UiO-67
• Chiral MOFs
• Asymmetric domino reactions
• Heterogeneous catalysis