Asymmetric Synthesis: Topics and Advances

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

Deadline for manuscript submissions: 31 July 2024 | Viewed by 2305

Special Issue Editor


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Guest Editor
Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, 1 Weigang Road, Xuanwu District, Nanjing 210095, China
Interests: catalytic asymmetric synthesis; heterocyclic skeleton construction; carbene chemistry; bioactive molecule design

Special Issue Information

Dear Colleagues,

For decades, the pursuit of efficient and simple methods to achieve the enantioselective synthesis of target products has been a hot field in chemistry. Traditional Lewis acid catalysis and transition-metal-catalyzed asymmetric synthesis (including cross-coupling reactions, carbene chemistry, hydrogenation reduction, etc.) have been considered and achieved remarkable results. Since 2000, research on the catalytic construction of central chiral and axial chiral compounds by small organic molecules has emerged and attracted much attention. In addition, the construction of chiral centers by new free radical reactions, developed in recent years, and catalytic asymmetric dearomatization reactions have also experienced notable progress. 

In the context of the vigorous development of the field of asymmetric synthesis, the journal Symmetry has set up a Special Issue called “Asymmetric Catalysis: Topics and Advances”, with the aim of collecting excellent papers in the fields of central chiral and axial chiral compound synthesis catalyzed by small organic molecules, Lewis acid catalysis, transition-metal-catalyzed asymmetric synthesis, asymmetric dearomatization, and asymmetric radical reactions. We warmly welcome chemists to publish their work in Symmetry

Please kindly note that all submitted papers should be within the scope of the journal where symmetry, or the deliberate lack of symmetry, is present.

Dr. Qiang Sha
Guest Editor

Manuscript Submission Information

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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

  • axial chirality
  • Lewis acid catalysis
  • transition metal catalysis
  • radical chemistry
  • asymmetric synthesis
  • symmetry

Published Papers (2 papers)

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Research

13 pages, 3276 KiB  
Article
A Stereoselective Entry to Enantiopure (S)-2-Amino-2-methyl-5-arylpent-4-ynoic Acids and Evaluation of Their Inhibitory Activity against Bacterial Collagenase G
by Hegine I. Hakobyan, Silva M. Jamgaryan, Armen S. Sargsyan, Yuri M. Danghyan, Vladimir A. Larionov, Victor I. Maleev, Ashot S. Saghyan and Zorayr Z. Mardiyan
Symmetry 2023, 15(10), 1924; https://doi.org/10.3390/sym15101924 - 16 Oct 2023
Viewed by 1023
Abstract
Nowadays, amino acids (AAs) and peptides with bulky side chains hold significant interest for organic synthesis and the modern pharma industry. Non-proteinogenic (or unnatural) AAs are key building blocks used for obtaining pharmaceutically relevant peptides and for the development of chiral molecular catalysts, [...] Read more.
Nowadays, amino acids (AAs) and peptides with bulky side chains hold significant interest for organic synthesis and the modern pharma industry. Non-proteinogenic (or unnatural) AAs are key building blocks used for obtaining pharmaceutically relevant peptides and for the development of chiral molecular catalysts, and they are extensively used in the total synthesis of complex natural compounds. Thus, an elaboration of cost-effective methods for the preparation of novel unnatural AAs to increase their structural diversity is highly desirable. In this context, herein, we present an asymmetric metal-templated synthesis of a number of enantiomerically pure (S)-2-amino-2-methyl-5-arylpent-4-ynoic acids starting from commercially available reagents and Belokon’s chiral auxiliary (S)-BPB, namely (S)-2-(N-benzylprolyl)aminobenzophenone. The construction of a chiral Ni(II) complex from alanine (Ala) and the subsequent propargylation, arylation by the Sonogashira cross-coupling reaction using various aryl halides, and, finally, an acidic decomposition of the obtained complexes deliver to the target complex α,α-disubstituted AAs featuring a triple bond in a side chain. Next, the Fmoc-protected α-AAs and dipeptide were synthesized. Finally, we examined the obtained α-AAs and peptide as collagenase inhibitors. Full article
(This article belongs to the Special Issue Asymmetric Synthesis: Topics and Advances)
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13 pages, 4897 KiB  
Communication
Reaction of Triazolic Aldehydes with Diisopropyl Zinc: Chirality Dissipation versus Amplification
by Oleg A. Mikhaylov, Elena Sh. Saigitbatalova, Liliya Z. Latypova, Almira R. Kurbangalieva and Ilya D. Gridnev
Symmetry 2023, 15(7), 1382; https://doi.org/10.3390/sym15071382 - 07 Jul 2023
Viewed by 767
Abstract
The phenomenon of amplifying asymmetric autocatalysis (AAA) has recently been restricted to alkylation of several specific substrates with diisopropyl zinc (Soai reaction). Targeting the extension of the scope of this phenomenon, we studied the reaction of triazolic aldehydes with diisopropyl zinc. Experiments demonstrated [...] Read more.
The phenomenon of amplifying asymmetric autocatalysis (AAA) has recently been restricted to alkylation of several specific substrates with diisopropyl zinc (Soai reaction). Targeting the extension of the scope of this phenomenon, we studied the reaction of triazolic aldehydes with diisopropyl zinc. Experiments demonstrated a diversity of results for the dissipation of chirality, conserving the existent ee and spontaneous chirality generation. Computational analysis showed that depending on the level of oligomerization of the catalyst, one could expect amplification (monomeric catalyst) while maintaining the existing chirality (dimeric catalyst) or dissipation of chirality (tetrameric catalyst). These findings are promising for the elaboration of synthetic protocols controlling chirality generation. In addition, three optically active triazolic alcohols were characterized. Full article
(This article belongs to the Special Issue Asymmetric Synthesis: Topics and Advances)
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