3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

Chiral macrocycles hold significant importance in various scientific fields due to their unique structural and chemical properties. By controlling their size, shape, and substituents, chiral macrocycles offer a platform for designing and synthesizing highly efficient catalysts, chemosensors, and functional materials. We have recently made strides in developing macrocyclic organocatalysts; however, their synthesis remains challenging. In this work, we aimed to discover a straightforward method for producing a diverse range of chiral macrocycles, thereby enabling further exploration in the field of interlocked and macrocyclic organocatalysts. We successfully established optimized synthetic routes for the synthesis of chiral macrocycles containing one or two stereogenic units, featuring varying ring sizes and substituents (21 examples in total).

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2025-08-28
DOI
https://doi.org/10.3762/bjoc.21.134
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

Christoph Wölper, Jan Riebe, Somayyeh Kheirjou, Maike Thiele et al.
Beilstein Journal of Organic Chemistry
Axial and Atropisomeric Chirality Synthesis
article

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

Christoph Wölper, Jan Riebe, Somayyeh Kheirjou, Maike Thiele, Jochen Niemeyer
article en

Abstract

Chiral macrocycles hold significant importance in various scientific fields due to their unique structural and chemical properties. By controlling their size, shape, and substituents, chiral macrocycles offer a platform for designing and synthesizing highly efficient catalysts, chemosensors, and functional materials. We have recently made strides in developing macrocyclic organocatalysts; however, their synthesis remains challenging. In this work, we aimed to discover a straightforward method for producing a diverse range of chiral macrocycles, thereby enabling further exploration in the field of interlocked and macrocyclic organocatalysts. We successfully established optimized synthetic routes for the synthesis of chiral macrocycles containing one or two stereogenic units, featuring varying ring sizes and substituents (21 examples in total).

Beilstein Journal of Organic ChemistryVol. 21
University of Duisburg-Essen (DE)
Alexander von Humboldt-Stiftung, Deutsche Forschungsgemeinschaft
Openalex Percentile: Top 83%
Axial and Atropisomeric Chirality Synthesis
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