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Related Concept Videos

Prochirality02:05

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 at Nitrogen, Phosphorus, and Sulfur02:30

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...
Molecules with Multiple Chiral Centers02:25

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...
Chirality in Nature02:30

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. The...
Chirality02:25

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 Compounds02:33

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,...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Inherently chiral resorcin[4]arenes: a new concept for improving the functionality.

Sebastian Wiegmann1, Jochen Mattay

  • 1Organische Chemie I, Fakultät für Chemie, Universität Bielefeld, Postfach 100131, 33501 Bielefeld, Germany.

Organic Letters
|May 20, 2011
PubMed
Summary

Researchers created a new reactive site on chiral resorcin[4]arenes by cleaving a methoxy group using 9-I-9-BBN. Chirality was preserved using a protecting group on the phenol.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Inherently chiral resorcin[4]arenes are valuable building blocks in supramolecular chemistry.
  • Functionalization of these molecules is crucial for developing new materials and catalysts.
  • The upper rim of resorcin[4]arenes presents a challenge for chemical modification due to unreactive groups.

Purpose of the Study:

  • To introduce a novel reactive position at the upper rim of inherently chiral resorcin[4]arenes.
  • To develop a method for selective functionalization while preserving inherent chirality.
  • To explore new synthetic routes for chiral macrocyclic compounds.

Main Methods:

  • Demethylation of a methoxy group at the upper rim of resorcin[4]arenes using 9-I-9-BBN (9-iodo-9-borabicyclo[3.3.1]nonane).
  • Protection of the free phenol group using a suitable protecting group to maintain structural integrity.
  • Characterization of the modified resorcin[4]arene using spectroscopic techniques.

Main Results:

  • Successful cleavage of the unreactive methoxy group, generating a new reactive hydroxyl (phenol) site.
  • Demonstration that the inherent chirality of the resorcin[4]arene framework is conserved during the reaction.
  • The use of a protecting group effectively prevented unwanted side reactions at the newly formed phenol.

Conclusions:

  • A new, reactive site has been successfully introduced onto the upper rim of inherently chiral resorcin[4]arenes.
  • This method provides a viable strategy for the selective functionalization of these chiral macrocycles.
  • The developed approach opens avenues for the synthesis of novel chiral materials and host-guest systems.