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Molecules
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Synthesis and Application of Atropisomeric Molecules
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Synthesis and Application of Atropisomeric Molecules

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

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 6111

Special Issue Editors

Dr. Wenling Qin

E-Mail Website
Guest Editor
School of Pharmaceutical Sciences, Chongqing University, Chongqing, China
Interests: organocatalysis; asymmetric synthesis
Dr. Gianpiero Cera

E-Mail Website
Guest Editor
Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A, I-43124 Parma, Italy
Interests: organometallic chemistry; organic chemistry; catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Atropisomeric molecules that bear a conformationally restrained stereogenic axis play enormous roles in natural products, medicines, catalysts, and material science. Their enantioselective synthesis and applications have witnessed dramatic developments over the past few years. Many elegant methodologies have been developed to atroposelectively access atropisomers containing rotationally restricted C-C bonds, including axially chiral (hetero)biaryls, axially chiral styrenes and their analogues. Beyond this, the molecular structure and function of other additional atropisomers containing axially chiral N-C(aryl) or N-N axes have attracted attention from communities. This Special Issue aims to provide a platform to highlight the recent advancements in this field of synthesis and applications of atropisomers in organic synthesis. Topics include but are not limited to asymmetric synthesis, functional development, and the structural analysis of all types of atropisomeric molecules. Communications, articles, and reviews regarding the abovementioned topics are warmly welcomed.

Dr. Wenling Qin
Dr. Gianpiero Cera
Guest Editors

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

  • atropisomisomers
  • axially chiral (hetero)biaryls
  • chiral styrene
  • C-N axis
  • N-N axis

Published Papers (4 papers)

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Research

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11 pages, 4091 KiB  
Article
Stereochemistry of N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones
by Arisa Chiba, Ryoko Tanaka, Mayuno Hotta, Kayo Nakamura, Kosho Makino, Hidetsugu Tabata, Tetsuta Oshitari, Hideaki Natsugari and Hideyo Takahashi
Molecules 2023, 28(12), 4734; https://doi.org/10.3390/molecules28124734 - 13 Jun 2023
Viewed by 827
Abstract
The stereochemical properties of N-acyl-5H-dibenzo[b,d]azepin-7(6H)-ones (2a–c), which inhibit potassium channels in T cells, were examined by freezing their conformational change due to 4-methyl substitution. N-Acyl-5H-dibenzo[b, [...] Read more.
The stereochemical properties of N-acyl-5H-dibenzo[b,d]azepin-7(6H)-ones (2a–c), which inhibit potassium channels in T cells, were examined by freezing their conformational change due to 4-methyl substitution. N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones exist as pairs of enantiomers [(a1R, a2R), (a1S, a2S)], and each atropisomer is separable at room temperature. An alternate procedure for preparing 5H-dibenzo[b,d]azepin-7(6H)-ones involves the intramolecular Friedel–Crafts cyclization of N-benzyloxycarbonylated biaryl amino acids. Consequently, the N-benzyloxy group was removed during the cyclization reaction to produce 5H-dibenzo[b,d]azepin-7(6H)-ones suitable for the subsequent N-acylation reaction. Full article
(This article belongs to the Special Issue Synthesis and Application of Atropisomeric Molecules)
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15 pages, 1486 KiB  
Article
Carbene-Catalyzed Atroposelective Annulation for Quick Access to Axially Chiral Thiazine Derivatives
by Xiaoqun Yang, Tingting Li, Jinli Chen, Yixian Huang, Tingwei Shen, Shiguang Li, Zhichao Jin and Shi-Chao Ren
Molecules 2023, 28(10), 4052; https://doi.org/10.3390/molecules28104052 - 12 May 2023
Cited by 1 | Viewed by 1289
Abstract
An N-heterocyclic carbene (NHC)-catalyzed atroposelective annulation reaction is disclosed for quick and efficient access to thiazine derivatives. A series of axially chiral thiazine derivatives bearing various substituents and substitution patterns were produced in moderate to high yields with moderate to excellent optical [...] Read more.
An N-heterocyclic carbene (NHC)-catalyzed atroposelective annulation reaction is disclosed for quick and efficient access to thiazine derivatives. A series of axially chiral thiazine derivatives bearing various substituents and substitution patterns were produced in moderate to high yields with moderate to excellent optical purities. Preliminary studies revealed that some of our products exhibit promising antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) that causes rice bacterial blight. Full article
(This article belongs to the Special Issue Synthesis and Application of Atropisomeric Molecules)
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29 pages, 4389 KiB  
Article
Atropostatin: Design and Total Synthesis of an Atropisomeric Lactone–Atorvastatin Prodrug
by Daniel Pecorari, Andrea Mazzanti and Michele Mancinelli
Molecules 2023, 28(7), 3176; https://doi.org/10.3390/molecules28073176 - 03 Apr 2023
Cited by 1 | Viewed by 1541
Abstract
Atorvastatins play an important role in the inhibition of HMG-CoA reductase, an enzyme present in the liver that takes part in the biosynthesis of cholesterol. In this article, we report the total synthesis of a lactone–atorvastatin prodrug with additional atropisomeric features. Conformational and [...] Read more.
Atorvastatins play an important role in the inhibition of HMG-CoA reductase, an enzyme present in the liver that takes part in the biosynthesis of cholesterol. In this article, we report the total synthesis of a lactone–atorvastatin prodrug with additional atropisomeric features. Conformational and experimental studies of model compounds were designed to test the stability of the chiral axis. Docking calculations were performed to evaluate the constant inhibition of a library of atorvastatins. Full synthesis of the best candidate was achieved and thermally stable atropisomeric lactone–atorvastatin was obtained. The absolute configuration of the chiral axis of the atropisomers was assigned by means of chiroptical ECD spectroscopy coupled with TD-DFT calculations. Full article
(This article belongs to the Special Issue Synthesis and Application of Atropisomeric Molecules)
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Review

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35 pages, 50152 KiB  
Review
Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions
by Wei-Yun Cai, Qian-Ni Ding, Ling Zhou and Jie Chen
Molecules 2023, 28(11), 4306; https://doi.org/10.3390/molecules28114306 - 24 May 2023
Cited by 2 | Viewed by 1758
Abstract
Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in [...] Read more.
Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in the asymmetric synthesis of biaryl/heterobiaryls atropisomers via construction of carbo- and hetero-cycles. This strategy has undoubtedly become and will continue to be a hot topic in the field of asymmetric synthesis and catalysis. This review aims to highlight the recent advancements in this field of atropisomer synthesis by using different organocatalysts in cycloaddition and cyclization strategies. The construction of each atropisomer, its possible mechanism, the role of catalysts, and its potential applications are illustrated. Full article
(This article belongs to the Special Issue Synthesis and Application of Atropisomeric Molecules)
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