Work

A non-helical supramolecular chiral catalyst for the asymmetric diels-alder reaction

Year: 2025

Type: article

Abstract: The research of supramolecular chiral catalyst morphology is critically important in asymmetric catalysis, yet current research predominantly focuses on helical architectures, with non-helical systems remaining underexplored. Herein, we present a new type of nanosheet (NS)-like supramolecular chiral catalyst self-assembled from L -threonine-based amphiphilie ( L -ThrC 16 ) and Cu(II), which achieves obvious asymmetric catalysis in the Diels-Alder reaction between aza-chalcone and cyclopentadiene (91% yield and 45% ee) despite its non-helical nanostructure. Compared with monomeric counterpart of L -ThrC 16 -Cu(II) catalyst displaying racemic product, the stronger interaction between aza-chalcone and L -ThrC 16 -NS-Cu(II) have been confirmed, which facilitates the chirality transfer from the supramolecular scaffold to aza-chalcone and thereby leading to enantioselectivity. This work not only challenges the conventional paradigm of helical dominance in chiral induction but also establishes a foundation for developing scalable, high-performance non-helical catalysts, thereby expanding the design principles for supramolecular asymmetric synthesis.

Source: Giant

DOI: 10.1016/j.giant.2025.100378