3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units
Somayyeh Kheirjou1, Jan Riebe1, Maike Thiele1
1Faculty of Chemistry (Organic Chemistry) and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, 45141 Essen, Germany.
Beilstein Journal of Organic Chemistry
|September 10, 2025
Summary
Researchers developed a straightforward synthesis for diverse chiral macrocycles, crucial for catalysis and materials science. This breakthrough simplifies the creation of complex molecules with one or two stereogenic units.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Chiral macrocycles are vital in catalysis, sensing, and materials science due to their tunable properties.
- Developing efficient synthetic routes for these complex molecules remains a significant challenge in organic chemistry.
Purpose of the Study:
- To discover a straightforward and versatile method for synthesizing a diverse array of chiral macrocycles.
- To enable further advancements in the field of interlocked and macrocyclic organocatalysts.
Main Methods:
- Optimization of synthetic routes for macrocycle formation.
- Incorporation of varying ring sizes and substituents.
- Synthesis of macrocycles with one or two stereogenic units.
Main Results:
- Successfully established optimized synthetic pathways for chiral macrocycle production.
- Generated a library of 21 diverse chiral macrocycles with controlled stereochemistry.
- Demonstrated the feasibility of producing macrocycles with varied ring sizes and substituents.
Conclusions:
- The developed synthetic method offers a simplified approach to accessing diverse chiral macrocycles.
- This work provides a foundation for exploring novel applications of chiral macrocycles in catalysis and materials science.
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