Issue 24, 2024

Nanoscale and chiral metal–organic frameworks for asymmetric reactions in water: bridging Lewis acid catalysis and biological systems

Abstract

Nowadays, stereoselective control over the sheer variety of chemical transformations benefits from the multipotency of chiral Lewis acids. Their use under biocompatible conditions has long posed a challenge because profuse amounts of biogenic nucleophiles readily deactivate them. To bridge the gap between chiral Lewis acid catalysis and biocompatible chemistry, the conversion of UiO(BPY)-type nanosized metal–organic frameworks (NMOFs) into chiral variants was herein exemplified. The combination of an elongated 2,2′-bipyridyl linker and scandium salt with a hydrophobic anion proved essential to implement traits such as robustness, biocompatibility, and catalytic activity. The catalyst could construct sufficiently hydrophobic environments sequestered within the framework, catalyzing asymmetric ring-opening reactions of meso-epoxide with low catalyst loading to afford β-amino acid alcohols in high yield (up to >99%) with high enantioselectivity (up to 88%). Most impressively, it exhibited a tolerance to the ex vivo poisoning of chiral Lewis acid catalysis by biogenic nucleophiles in sharp contrast to conventional water-compatible Lewis acids.

Graphical abstract: Nanoscale and chiral metal–organic frameworks for asymmetric reactions in water: bridging Lewis acid catalysis and biological systems

Supplementary files

Article information

Article type
Edge Article
Submitted
27 feb. 2024
Accepted
05 may. 2024
First published
06 may. 2024
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., 2024,15, 9120-9126

Nanoscale and chiral metal–organic frameworks for asymmetric reactions in water: bridging Lewis acid catalysis and biological systems

W. Srimontree, T. Kitanosono, Y. Yamashita and S. Kobayashi, Chem. Sci., 2024, 15, 9120 DOI: 10.1039/D4SC01343C

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