Supramolecular Double-Helical Polymers: Supramolecular Chiral Induction and Asymmetric Catalysis

Seeking a supramolecular chiral system induced by trace chiral molecules instead of traditional complex and expensive chiral ligands to achieve high yield or ee value conversion of the products is of great significance in asymmetric synthesis but still remains a challenge. Herein, two types of double helical supramolecular chiral systems, (<i>M</i>)-<b>Helix</b> and (<i>P</i>)-<b>Helix</b>, with opposite chiral optics were constructed in situ using tyrosine-functionalized pillar[5]arene as inducers. These systems exhibit chiroptical stability and enable remarkable chirality amplification from 7 mol% chiral seeds. When applied to intermolecular olefin cyano-trifluoromethylation, (<i>M</i>)-<b>Helix</b> exhibits remarkable catalytic efficiency (yield up to 89%), whereas (<i>P</i>)-<b>Helix</b> achieves higher enantioselectivity (ee up to 84%). This research will provide new ideas for supramolecular chiral catalysts in organic asymmetric catalysis applications.

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Publication Details

Journal
Molecules
Published
2025-03-28
DOI
https://doi.org/10.3390/molecules30071517
Citations
3
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
2.81

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article

Supramolecular Double-Helical Polymers: Supramolecular Chiral Induction and Asymmetric Catalysis

Xinyu Jia, Luzhi Liu, Yan Huang, Qin He et al.
3 citations
Molecules
Synthesis and Properties of Aromatic Compounds
2.81
article

Supramolecular Double-Helical Polymers: Supramolecular Chiral Induction and Asymmetric Catalysis

Xinyu Jia, Luzhi Liu, Yan Huang, Qin He, Wengui Duan, Yanjun Zhang, Xiaojun Guo
article en
3 citations

Abstract

Seeking a supramolecular chiral system induced by trace chiral molecules instead of traditional complex and expensive chiral ligands to achieve high yield or ee value conversion of the products is of great significance in asymmetric synthesis but still remains a challenge. Herein, two types of double helical supramolecular chiral systems, (<i>M</i>)-<b>Helix</b> and (<i>P</i>)-<b>Helix</b>, with opposite chiral optics were constructed in situ using tyrosine-functionalized pillar[5]arene as inducers. These systems exhibit chiroptical stability and enable remarkable chirality amplification from 7 mol% chiral seeds. When applied to intermolecular olefin cyano-trifluoromethylation, (<i>M</i>)-<b>Helix</b> exhibits remarkable catalytic efficiency (yield up to 89%), whereas (<i>P</i>)-<b>Helix</b> achieves higher enantioselectivity (ee up to 84%). This research will provide new ideas for supramolecular chiral catalysts in organic asymmetric catalysis applications.

MoleculesVol. 30(7)
Guangxi University (CN), Beibu Gulf University (CN), Guangxi University of Chinese Medicine (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 11%
Synthesis and Properties of Aromatic Compounds
2.81
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