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Molecules
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Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules
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Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 30 June 2024 | Viewed by 7932

Special Issue Editor

Prof. Dr. Giorgio Bencivenni

E-Mail Website
Guest Editor
University of Bologna, Italy

Special Issue Information

Dear Colleagues,

In recent years, compounds containing a stereogenic axis as an element of chirality have received a huge amount of attention due to their important role as catalysts or ligands for asymmetric synthesis and biological active compounds, the latter mainly obtained from natural sources. Using both metal and organocatalytic methodologies, enormous progress has been achieved in their enantioselective synthesis. In particular, the development of innovative reactions, which could give easy access to structurally diverse axially chiral compounds, has produced an unprecedented number of unique classes of axially enantioenriched backbones. The broad applicability of axially chiral compounds, not only in the abovementioned fields, but also in the material and pharmacological sciences, make their synthesis a continuous and fascinating challenge for the chemist community.

This Special Issue will focus on recent developments in the synthesis, application, as well as characterization of novel structures of compounds falling into the definition of axially chiral compounds, such as atropisomers, allenes, alkylidenes, spiranes, and so on.

Prof. Giorgio Bencivenni
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Atroposelective synthesis
  • Ligands
  • Catalysts
  • Chiral allenes
  • Chiral alkylidenes
  • Axially chiral spiro compounds
  • Atropisomers
  • Desymmetrization
  • Kinetic resolution
  • Dynamic kinetic resolution
  • C–H activation
  • Asymmetric coupling reaction
  • Rotational barrier
  • Dynamic thermodynamic resolution
  • Chiroptical properties
  • Natural products

Published Papers (5 papers)

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Research

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13 pages, 4304 KiB  
Article
On the Nature of the Rotational Energy Barrier of Atropisomeric Hydrazides
by Andrea Pellegrini, Laura Marcon, Paolo Righi, Giovanni Centonze, Chiara Portolani, Marco Capodiferro, Shilashi Badasa Oljira, Simone Manetto, Alessia Ciogli and Giorgio Bencivenni
Molecules 2023, 28(23), 7856; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28237856 - 29 Nov 2023
Viewed by 1312
Abstract
N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric hydrazides, combining an experimental and computational approach. The [...] Read more.
N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric hydrazides, combining an experimental and computational approach. The focus is on examining how electronic and steric factors impact the racemization process. The results obtained indicate that the barrier observed during the racemization process mainly arises from an increase in the p-orbital character of the nitrogen atoms. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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14 pages, 1458 KiB  
Article
A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols
by Lei Shi, Jiawei Zhu, Biqiong Hong and Zhenhua Gu
Molecules 2023, 28(16), 5956; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28165956 - 08 Aug 2023
Viewed by 847
Abstract
We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic tBuOK/air atmosphere and an acidic NaClO/n-Bu4NHSO4, were developed to oxidatively cleave [...] Read more.
We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic tBuOK/air atmosphere and an acidic NaClO/n-Bu4NHSO4, were developed to oxidatively cleave the C-C bond, resulting in the formation of axially chiral biaryl diketones. Finally, brief synthetic applications of the obtained chiral aryl diketones were demonstrated. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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17 pages, 4108 KiB  
Article
Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies
by Alessia Ciogli, Andrea Fochetti, Andrea Sorato, Giancarlo Fabrizi, Nunzio Matera, Andrea Mazzanti and Michele Mancinelli
Molecules 2023, 28(13), 4915; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28134915 - 22 Jun 2023
Viewed by 936
Abstract
The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and [...] Read more.
The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and configurations were derived using NOESY-1D experiments. Depending on the energies related to the conformational exchange, the experimental energy barriers were determined through Dynamic NMR, Dynamic HPLC or kinetic studies. The atropisomeric pairs were resolved in the latter scenario, and their absolute configuration was assigned using the ECD/TD-DFT method. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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14 pages, 2685 KiB  
Article
Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents
by Ji-Wei Zhang, Shao-Hua Xiang, Shaoyu Li and Bin Tan
Molecules 2021, 26(11), 3223; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26113223 - 27 May 2021
Cited by 4 | Viewed by 3031
Abstract
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [...] Read more.
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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Review

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19 pages, 5784 KiB  
Review
Synthesis and Structural and Optical Behavior of Dehydrohelicene-Containing Polycyclic Compounds
by Md. Imrul Khalid, Mohamed S. H. Salem and Shinobu Takizawa
Molecules 2024, 29(2), 296; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29020296 - 05 Jan 2024
Viewed by 997
Abstract
Dehydrohelicene-based molecules stand out as highly promising scaffolds and captivating chiroptical materials, characterized by their unique chirality. Their quasi-helical π-conjugated molecular architecture, featuring successively ortho-annulated aromatic rings, endows them with remarkable thermal stability and optical properties. Over the past decade, diverse approaches [...] Read more.
Dehydrohelicene-based molecules stand out as highly promising scaffolds and captivating chiroptical materials, characterized by their unique chirality. Their quasi-helical π-conjugated molecular architecture, featuring successively ortho-annulated aromatic rings, endows them with remarkable thermal stability and optical properties. Over the past decade, diverse approaches have emerged for synthesizing these scaffolds, reinvigorating this field, with anticipated increased attention in the coming years. This review provides a comprehensive overview of the historical evolution of dehydrohelicene chemistry since the pioneering work of Zander and Franke in 1969 and highlights recent advancements in the synthesis of various molecules incorporating dehydrohelicene motifs. We elucidate the intriguing structural features and optical merits of these molecules, occasionally drawing comparisons with their helicene or circulene analogs to underscore the significance of the bond between the helical termini. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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