Issue 12, 2022

Chiral proline-substituted porous organic cages in asymmetric organocatalysis

Abstract

The efficient preparation of chiral porous organic cages (POCs) with specific functions is challenging, and their application in asymmetric catalysis has not previously been explored. In this work, we have achieved the construction of chiral POCs based on a supramolecular tetraformyl-resorcin[4]arene scaffold with different chiral proline-modified diamine ligands and utilizing dynamic imine chemistry. The incorporation of V-shaped or linear chiral diamines affords the [4 + 8] square prism and [6 + 12] octahedral POCs respectively. The appended chiral proline moieties in such POCs make them highly active supramolecular nanoreactors for asymmetric aldol reactions, delivering up to 92% ee. The spatial distribution of chiral catalytic sites in these two types of POCs greatly affects their catalytic activities and enantioselectivities. This work not only lays a foundation for the asymmetric catalytic application of chiral POCs, but also contributes to our understanding of the catalytic function of biomimetic supramolecular systems.

Graphical abstract: Chiral proline-substituted porous organic cages in asymmetric organocatalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
21 1 2022
Accepted
03 3 2022
First published
03 3 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 3582-3588

Chiral proline-substituted porous organic cages in asymmetric organocatalysis

N. Xu, K. Su, E. M. El-Sayed, Z. Ju and D. Yuan, Chem. Sci., 2022, 13, 3582 DOI: 10.1039/D2SC00395C

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