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Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Chirality

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

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Related Experiment Video

Updated: Jun 5, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Advances in Chiral Macrocycles: Molecular Design and Applications.

Zhihong Sun¹, Hao Tang¹, Lingyun Wang¹

¹State Key Laboratory of Luminescent Materials and Devices, Department of Chemistry, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510641, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|December 14, 2024

Summary

Chiral macrocycles offer advanced applications in molecular recognition and catalysis. Their unique structures enable precise control over enantioselective processes and circularly polarized luminescence (CPL).

Keywords:

Asymmetric catalysis Chiral macrocycles Circularly polarized luminescence Enantioselective recognition

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

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Last Updated: Jun 5, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Published on: February 7, 2019

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Chiroptical Materials

Background:

Chiral macrocycles are increasingly recognized for their potential in enantioselective applications.
Their terminal-free structure, preorganized chiral cavities, and self-assembly properties are key advantages.
Applications span asymmetric catalysis, molecular recognition, and circularly polarized luminescence (CPL).

Purpose of the Study:

To review recent advancements in the design and synthesis of chiral macrocycles.
To highlight strategies for constructing macrocycles with diverse chiral elements (central, axial, helical, planar).
To discuss the application of these macrocycles in optoelectronic and catalytic systems.

Main Methods:

Review of literature on chiral macrocycle synthesis and applications.
Categorization of chiral macrocycles based on their type of chirality.
Analysis of structure-property relationships, focusing on rigidity-flexibility balance.

Main Results:

Summary of diverse chiral macrocycle architectures and their synthesis.
Demonstration of tailored chiroptical properties based on chirality type.
Examples of successful applications in catalysis and CPL devices.

Conclusions:

Chiral macrocycles are versatile platforms for advanced chemical applications.
Optimizing the balance between rigidity and flexibility is crucial for performance.
Future research holds promise for novel designs and expanded applications in chiral technologies.