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Symmetry
Special Issues
Novel Approaches for Asymmetric Synthesis
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Novel Approaches for Asymmetric Synthesis

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 10270

Special Issue Editors

Dr. Veroniki Peter Vidali

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Guest Editor
Institute of Nanoscience and Nanotechnology, National Centre of Scientific Research “Demokritos”, 15310 Athens, Greece
Interests: organic synthesis; medicinal and pharmaceutical chemistry; synthetic organic chemistry; synthesis; heterocyclic chemistry; organic chemistry synthesis; synthetic chemistry; natural product chemistry; organometallics; nuclear magnetic resonance
Dr. Marina Sagnou

E-Mail Website
Guest Editor
National Centre for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 15310 Athens, Greece
Interests: medicinal and pharmaceutical chemistry; synthesis; organic synthesis; DNA damage, apoptosis, pharmaceutical chemistry; pharmacology radioactivity; synthetic organic chemistry; heterocyclic chemistry
Dr. Gerasimos Rassias

E-Mail Website
Guest Editor
Department of Chemistry, University of Patras, 26504 Patras, Greece
Interests: medicinal chemistry (lead optimization for antiviral, oncology and CNS targets); 2nd generation processes for improving the synthesis of drug molecules (original and generic); green chemistry; asymmetric synthesis; metal- and organocatalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Chirality is one of the most important structural features of organic compounds. Naturally occurring molecules exhibit different bioactivities depending on their enantiomeric forms. This behaviour is crucial for the production of high-value pharmaceuticals and agrochemicals. Moreover, chiral phenomena play a vital role in nanotechnology applications, and many nanotech innovations benefit greatly from molecular chirality, e.g., molecular switches, nanotubes, and others.

Many asymmetric approaches have been developed. The use of abundant chiral sources, e.g., sugars, induction of chirality via an auxiliary or a catalyst, or the use of enzymes, are some of them. However, over the past few decades, the need for enantiomerically pure or enriched compounds continues to increase. Thus, the field of asymmetric synthesis is one of the most dynamic areas in chemical research, at the academic and industrial level. 

The present Special Issue aims to highlight novel approaches in the area of asymmetric synthesis. Powerful chemical transformations, the use of unprecedented catalysts or enzymes, and methods of low cost and waste are only some of the subjects we are soliciting from researchers to contribute (research and review articles).

Submit your paper and select the Journal “Symmetry” and the Special Issue “Novel Approaches for Asymmetric Synthesis” via: MDPI submission system. Our papers will be published on a rolling basis and we will be pleased to receive your submission once you have finished it.

Dr. Veroniki Peter Vidali
Dr. Marina Sagnou
Prof. Gerasimos Rassias
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. 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

  • Catalysts for asymmetric synthesis
  • New chiral sources with applications in asymmetric synthesis
  • Auxiliaries for induction of chirality
  • Enzymes used in asymmetric approaches
  • Green reagents for applications in asymmetric synthetic methods
  • Asymmetric synthesis of natural products or analogues
  • Applications of asymmetric synthesis in medicine, agrochemical, nanotechnology, and others

Published Papers (3 papers)

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Research

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11 pages, 1400 KiB  
Article
Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine N-Oxide with Benzyl Methyl Ketone
by Zuzanna Wrzeszcz, Jakub A. Warachim and Renata Siedlecka
Symmetry 2024, 16(1), 104; https://doi.org/10.3390/sym16010104 - 15 Jan 2024
Viewed by 740
Abstract
The asymmetric formal [3 + 3] annulation process of (E)-2-(3-phenylacryloyl)pyridine N-oxide with benzyl methyl ketone was investigated. The possibility of a stereoselective outcome was checked using salts of natural amino acids, as well as chiral bifunctional derivatives containing amino groups [...] Read more.
The asymmetric formal [3 + 3] annulation process of (E)-2-(3-phenylacryloyl)pyridine N-oxide with benzyl methyl ketone was investigated. The possibility of a stereoselective outcome was checked using salts of natural amino acids, as well as chiral bifunctional derivatives containing amino groups and thiourea or squaramide fragments as organocatalysts. Different types of organocatalysts applied led to opposite enantiomers of 2-(3-oxo-4,5-diphenyl-cyclohex-1-en-yl)pyridine 1-oxide (up to 60% ee). Spectroscopic analysis of the isolated product and analysis of the reaction course was carried out, taking into account the obtained regio- and stereoselectivity. In order to verify the postulated results, calculations of the energy of the intermediate reaction products and the final product using the Kohn–Sham Density Functional Theory (KS-DFT) were made. Full article
(This article belongs to the Special Issue Novel Approaches for Asymmetric Synthesis)
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15 pages, 2581 KiB  
Article
Organocatalytic Asymmetric Halocyclization of Allylic Amides to Chiral Oxazolines Using DTBM-SEGPHOS—Mechanistic Implications from Hammett Plots
by Fotini Moschona, Christina Misirlaki, Nikolaos Karadimas, Maria Koutiva, Ioanna Savvopoulou and Gerasimos Rassias
Symmetry 2022, 14(5), 989; https://doi.org/10.3390/sym14050989 - 12 May 2022
Viewed by 3878
Abstract
The intramolecular halocyclization of alkenes possessing an internal heteroatom nucleophile leads to multifunctional heterocycles which are useful versatile intermediates in organic synthesis. The asymmetric chlorocyclisation of 2-substituted allylic amides gives access to chiral oxazolines bearing a chloromethyl moiety for further synthetic manipulation. The [...] Read more.
The intramolecular halocyclization of alkenes possessing an internal heteroatom nucleophile leads to multifunctional heterocycles which are useful versatile intermediates in organic synthesis. The asymmetric chlorocyclisation of 2-substituted allylic amides gives access to chiral oxazolines bearing a chloromethyl moiety for further synthetic manipulation. The literature reports on this transformation involve complex syntheses of the 2-substituted allylic amides and cryogenic temperatures for achieving high enantioselectivities in the organocatalyzed halocyclization step. Based on the Heck reaction of aryl bromides and Boc-protected allylamine or allylamine benzamides, we developed a practical synthesis of 2-substituted allylic amides that does not require chromatography and accomplished their asymmetric halocyclization reaction with 24–92%ee under practical conditions (5 °C, CpME) catalyzed by (S)-(+)-DTBM-SEGPHOS. In addition, using appropriately substituted substrates, we generated Hammett plots and formulated a consistent mechanism for the halocyclization reaction which involves two competing modes of formation of the haliranium intermediate whose relative kinetics are governed by the electronic properties of the substrate. Full article
(This article belongs to the Special Issue Novel Approaches for Asymmetric Synthesis)
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Review

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22 pages, 8141 KiB  
Review
Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases
by Raffaella Ferraccioli
Symmetry 2021, 13(9), 1744; https://doi.org/10.3390/sym13091744 - 19 Sep 2021
Cited by 6 | Viewed by 4243
Abstract
Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) of racemic chiral alcohols is a general and practical process to obtain the corresponding enantiopure esters R with quantitative conversion. The use of known Ru-catalysts as well as newly developed homogeneous and heterogeneous metal catalysts (Fe, V) [...] Read more.
Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) of racemic chiral alcohols is a general and practical process to obtain the corresponding enantiopure esters R with quantitative conversion. The use of known Ru-catalysts as well as newly developed homogeneous and heterogeneous metal catalysts (Fe, V) contributed to make the DKR process more sustainable and to expand the substrate scope of the reaction. In addition to classical substrates, challenging allylic alcohols, tertiary alcohols, C1-and C2-symmetric biaryl diols turned out to be competent substrates. Synthetic utility further emerged from the integration of this methodology into cascade reactions leading to linear/cyclic chiral molecules with high ee through the formation of multiple bonds, in a one-pot procedure. Full article
(This article belongs to the Special Issue Novel Approaches for Asymmetric Synthesis)
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