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

alpha, alpha-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.

Automated summary

In this study, alpha, alpha-L-Diaryl prolinol was immobilized into a highly stable porous MOF, UiO-67, via 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 enantioselective reactions, as well as good reusability with recycle use for three times without significant loss of activity. This research represents the first report of chiral MOFs as heterogeneous catalysts for asymmetric domino reactions.