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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...

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...

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...

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,...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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.

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Related Experiment Video

Updated: Sep 22, 2025

Fabrication Procedures and Birefringence Measurements for Designing Magnetically Responsive Lanthanide Ion Chelating Phospholipid Assemblies

Fabrication Procedures and Birefringence Measurements for Designing Magnetically Responsive Lanthanide Ion Chelating Phospholipid Assemblies

Published on: January 3, 2018

BINOL as a chiral element in mechanically interlocked molecules.

Matthias Krajnc¹, Jochen Niemeyer¹

¹Faculty of Chemistry (Organic Chemistry) and Centre of Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstr. 7, 45141 Essen, Germany.

Beilstein Journal of Organic Chemistry

|May 23, 2022

Summary

Axially chiral 1,1'-binaphthyl-2,2'-diol (BINOL) units create stereogenic elements in chiral mechanically interlocked molecules (MIMs). These BINOL-based MIMs show promise in asymmetric catalysis and stereoselective sensing.

Keywords:

BINOL axial chirality catenanes interlocked molecules rotaxanes

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Published on: March 24, 2018

Area of Science:

Supramolecular Chemistry
Organic Chemistry
Stereochemistry

Background:

Mechanically Interlocked Molecules (MIMs) are complex architectures with unique topological properties.
Axially chiral 1,1'-binaphthyl-2,2'-diol (BINOL) is a privileged chiral scaffold widely used in asymmetric synthesis.
Integrating chiral units into MIMs is crucial for developing advanced stereoselective systems.

Purpose of the Study:

To review the synthesis and properties of BINOL-based chiral MIMs.
To highlight the utility of these chiral MIMs in diastereoselective modifications.
To explore their applications in asymmetric catalysis and stereoselective chemosensing.

Main Methods:

Synthesis of BINOL-based mechanically interlocked molecules.
Characterization of their structural and stereochemical properties.
Evaluation of their performance in catalytic and sensing applications.

Main Results:

Successful incorporation of the BINOL unit as a stereogenic element in various MIM architectures.
Demonstration of diastereoselective transformations facilitated by these chiral MIMs.
Evidence of their efficacy in asymmetric catalysis and chiral recognition.

Conclusions:

BINOL-based chiral MIMs represent a powerful platform for stereochemical control.
Their unique structure enables diverse applications in catalysis and sensing.
This field is poised for significant growth and innovation in supramolecular chemistry.