Asymmetry and Symmetry in Organic Chemistry 2021

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 6156

Special Issue Editor


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Guest Editor
Department of Organic & Applied Chemistry, University of Łódź, Łódź, Poland
Interests: organic synthesis; heterocyclic and heteroatom chemistry; sulfur organic chemistry; asymmetric synthesis using chiral catalysts; stereochemistry; use of enzymes in organic synthesis; chemistry of aziridines
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Special Issue Information

Dear Colleagues,

Stereoselective construction of new organic compounds is still one of the most important fields in modern synthetic organic chemistry. This Special Issue invites contributions concerning asymmetric synthesis, especially including the application of chiral ligands and organocatalysts, various theoretical aspects of the optical activity of organic compounds, stereodivergent and stereoconvergent catalysis, and mechanistic aspects of asymmetric induction. As part of this Special Issue, various synthetic approaches leading to symmetric organic compounds are also welcome. They may include, for example, the synthesis of molecules bearing a plane of symmetry, symmetry axis, center of symmetry, or similar.

Prof. Dr. Michal Rachwalski
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. Symmetry is an international peer-reviewed open access monthly 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 2400 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

  • asymmetric synthesis
  • asymmetric induction
  • chiral ligands
  • chiral organocatalysts
  • elements of symmetry
  • stereoconvergent catalysis
  • stereodivergent catalysis
  • symmetric organic compounds

Published Papers (4 papers)

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Editorial

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2 pages, 155 KiB  
Editorial
Special Issue: Asymmetry and Symmetry in Organic Chemistry
by Michał Rachwalski
Symmetry 2023, 15(7), 1363; https://doi.org/10.3390/sym15071363 - 4 Jul 2023
Cited by 1 | Viewed by 3709
Abstract
In organic chemistry, the concepts of asymmetry and symmetry play crucial roles in understanding the properties and reactivity of molecules [...] Full article
(This article belongs to the Special Issue Asymmetry and Symmetry in Organic Chemistry 2021)

Research

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15 pages, 1661 KiB  
Article
Design, Synthesis, and In Vitro Antiproliferative Screening of New Hydrazone Derivatives Containing cis-(4-Chlorostyryl) Amide Moiety
by Tarfah Al-Warhi, Leena S. Alqahtani, Matokah Abualnaja, Saba Beigh, Ola A. Abu Ali, Fahmy G. Elsaid, Ali A. Shati, Rasha Mohammed Saleem, Ali Hassan Ahmed Maghrabi, Amani Abdulrahman Alharthi, Amal Alyamani, Eman Fayad, Ali H. Abu Almaaty, Islam Zaki and Shaimaa Hamouda
Symmetry 2022, 14(11), 2457; https://doi.org/10.3390/sym14112457 - 19 Nov 2022
Cited by 5 | Viewed by 1522
Abstract
Hydrazones are regarded as a distinctive category of organic compounds because of their tremendous characteristics and potential uses in analytical, chemical, and medicinal chemistry. In the present study, a new series of Hydrazone Derivatives bearing cis-(4-chlorostyryl) amide moiety were designed and synthesized. [...] Read more.
Hydrazones are regarded as a distinctive category of organic compounds because of their tremendous characteristics and potential uses in analytical, chemical, and medicinal chemistry. In the present study, a new series of Hydrazone Derivatives bearing cis-(4-chlorostyryl) amide moiety were designed and synthesized. In vitro cytotoxicity screening showed that compounds 3i, 3l, 3m, and 3n revealed potent anticancer activity against MCF-7 cancer cell line with IC50 values between 2.19–4.37 μM compared with Staurosporin as a reference compound. The antiproliferative activity of these compounds appears to be correlated well with their ability to inhibit the VEGFR-2 kinase enzyme. Activation of the damage response pathway leads to cellular cycle arrest at the G1 phase. Fluorochrome Annexin V/PI staining indicated that cell death proceeds through the apoptotic pathway mechanism. The mechanistic pathway was confirmed by a significant increase in the level of active caspase 9 compared with control untreated MCF-7 cells. Full article
(This article belongs to the Special Issue Asymmetry and Symmetry in Organic Chemistry 2021)
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15 pages, 47767 KiB  
Article
Racemic and Meso Crystal Structures of an Axial-Chiral Spirobi-(dinaphthoazepin)ium Salt: Emergence of an S4-Symmetric Molecule
by Philipp Honegger, Natalie Gajic, Alexander Prado-Roller and Michael Widhalm
Symmetry 2021, 13(8), 1365; https://doi.org/10.3390/sym13081365 - 27 Jul 2021
Cited by 1 | Viewed by 1675
Abstract
To date, only a few instances of S4-symmetric organic molecules exist. In principle, spirobi-(dinaphthoazepin)ium cations can achieve this highly symmetric point group. Heating racemic 2,2′-bis(bromomethyl)-1,1′binaphthyl with aqueous ammonia afforded a mixture of rac- and meso-3,3′,5,5′-tetrahydro-4,4′-spirobi[dinaphtho[2,1-c:1′,2′-e]azepin]-4-ium bromide which was separated [...] Read more.
To date, only a few instances of S4-symmetric organic molecules exist. In principle, spirobi-(dinaphthoazepin)ium cations can achieve this highly symmetric point group. Heating racemic 2,2′-bis(bromomethyl)-1,1′binaphthyl with aqueous ammonia afforded a mixture of rac- and meso-3,3′,5,5′-tetrahydro-4,4′-spirobi[dinaphtho[2,1-c:1′,2′-e]azepin]-4-ium bromide which was separated by fractional crystallisation. Both stereoisomers were characterised spectroscopically, and their crystal structures were determined and compared. The rac crystal structure differs significantly from the known enantiopure one. The meso molecules display a near-perfect S4 symmetry. Upon treatment with KOtBu, both isomers undergo Stevens rearrangement. Full article
(This article belongs to the Special Issue Asymmetry and Symmetry in Organic Chemistry 2021)
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Review

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13 pages, 1163 KiB  
Review
C2-Symmetric N-Heterocyclic Carbenes in Asymmetric Transition-Metal Catalysis
by Chiara Costabile, Stefania Pragliola and Fabia Grisi
Symmetry 2022, 14(8), 1615; https://doi.org/10.3390/sym14081615 - 5 Aug 2022
Cited by 2 | Viewed by 1877
Abstract
The last decades have witnessed a rapid growth of applications of N-heterocyclic carbenes (NHCs) in different chemistry fields. Due to their unique steric and electronic properties, NHCs have become a powerful tool in coordination chemistry, allowing the preparation of stable metal-ligand frameworks [...] Read more.
The last decades have witnessed a rapid growth of applications of N-heterocyclic carbenes (NHCs) in different chemistry fields. Due to their unique steric and electronic properties, NHCs have become a powerful tool in coordination chemistry, allowing the preparation of stable metal-ligand frameworks with both main group metals and transition metals. An overview on the use of five membered monodentate C2-symmetric N-heterocyclic carbenes (NHCs) as ligands for transition-metal complexes and their most relevant applications in asymmetric catalysis is offered. Full article
(This article belongs to the Special Issue Asymmetry and Symmetry in Organic Chemistry 2021)
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