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Chiral medium-sized rings beyond central chirality.
Shiqi Jia1, Yudong Hao2, Yuedi Li2
1Department of Chemistry, Zhengzhou University, Zhengzhou, China. jiashiqi17@zzu.edu.cn.
Nature Reviews. Chemistry
|July 14, 2025
Summary
This review explores unconventional chirality in medium-sized rings (MSRs), focusing on axial, inherent, and planar types. It details synthetic strategies and conformational stability factors for these important bioactive molecules.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Stereochemistry
Background:
- Medium-sized rings (MSRs) are crucial structural motifs in many bioactive molecules.
- While central chirality in MSRs is well-studied, unconventional chiral types remain underexplored.
- Unconventional chirality includes axial, inherent, and planar chirality.
Purpose of the Study:
- To review recent advances in the synthesis of MSRs with unconventional chirality.
- To critically evaluate the advantages and limitations of various synthetic strategies.
- To discuss factors influencing the conformational stability of chiral MSRs.
Main Methods:
- Literature review of synthetic methodologies for chiral MSRs.
- Analysis of structure and energy to understand conformational stability.
- Critical evaluation of synthetic routes and their applicability.
Main Results:
- Significant progress has been made in synthesizing MSRs with axial, inherent, and planar chirality over the past decade.
- Key synthetic strategies for each type of unconventional chirality have been identified.
- Factors affecting conformational stability, such as ring size and substitution patterns, have been elucidated.
Conclusions:
- Chiral MSRs with unconventional chirality represent a promising area for drug discovery.
- Further research into their synthesis and conformational properties will unlock new applications.
- This review provides a comprehensive overview for researchers in the field.
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