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Prochirality

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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...

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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...

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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. The...

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Updated: Jul 18, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Chiral recognition in cucurbituril cavities.

Mikhail V Rekharsky¹, Hatsuo Yamamura, Chika Inoue

¹Entropy Control Project, ICORP, JST, 4-6-3 Kamishinden, Toyonaka 560-0085, Japan.

Journal of the American Chemical Society

|November 16, 2006

Summary

Achiral cucurbiturils (CBs) achieve high enantioselectivity using chiral binders. This breakthrough in supramolecular chemistry enables unprecedented discrimination of chiral molecules.

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Area of Science:

Supramolecular Chemistry
Chiral Recognition
Host-Guest Chemistry

Background:

Achiral cucurbiturils (CBs) are macrocyclic hosts with limited ability for chiral discrimination.
Developing methods for enantioselective recognition using achiral hosts is a significant challenge in chemistry.

Purpose of the Study:

To engineer achiral cucurbiturils for significant enantiomeric and diastereomeric discrimination.
To investigate the mechanism of chiral recognition by modified CB hosts.

Main Methods:

Utilized cucurbituril [6] (CB[6]) and cucurbituril [7] (CB[7]) as host molecules.
Incorporated chiral amine binders, specifically (R)- or (S)-2-methylpiperazine, to create chiral supramolecular hosts.
Employed calorimetric, nuclear magnetic resonance (NMR), light-scattering, and mass spectrometry for analysis.

Main Results:

Achiral CB[6] hosts functionalized with chiral binders achieved 95% enantioselectivity for (S)-2-methylbutylamine.
This represents the highest enantioselectivity reported for supramolecular systems derived from achiral hosts.
CB[7] demonstrated up to 8-fold higher diastereoselectivity for dipeptides, such as L-Phe-L-Leu-NH3+ versus L-Phe-D-Leu-NH3+.

Conclusions:

Incorporating strong chiral binders into achiral cucurbiturils effectively imparts significant enantiomeric and diastereomeric discrimination capabilities.
This strategy provides a novel and highly efficient approach for chiral recognition in supramolecular chemistry.
The findings open new avenues for designing advanced chiral sensors and separation materials.