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Journals
Catalysts
Special Issues
Organocatalytic Asymmetric Synthesis or Transformation of Heterocycles
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Organocatalytic Asymmetric Synthesis or Transformation of Heterocycles

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (30 September 2021) | Viewed by 8192

Special Issue Editors

Dr. Sylvain Oudeyer

E-Mail Website
Guest Editor
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France
Interests: asymmetric catalysis; ion pairing catalysis; phase-transfer catalysis; organocatalysis; heterocycle synthesis
Dr. Jean-François Brière

E-Mail Website
Co-Guest Editor
Normandie Univ, UNIROUEN, INSA Rouen, CNRS, COBRA, 76000 Rouen, France
Interests: organocatalyzed synthesis of chiral biorelevant heterocycles; asymmetric synthesis; useful platforms in multicomponent synthesis

Special Issue Information

Dear Colleagues,

Since its revival in the late 1990’s, organocatalysis has received tremendous attention from the organic chemistry community, elevating this strategy, along with metal and enzyme catalysis, as one of the three pillars of catalysis. During the last 20 years, several modes of activation have been developed, encompassing covalent and non-covalent approaches, affording a unique opportunity to have access to a large array of chiral molecules with a high level of stereo-induction. In that context, the organocatalyzed construction of heterocycles has become a method of choice of these ubiquitous core architectures in drugs or naturally-occurring products.
This Special Issue intends to highlight some of the recent work in the enantioselective synthesis or transformation of heterocycles involving organocatalytic approaches. Submissions are welcome in the form of original research papers or short reviews that reflect the state of the art of this research area.

Dr. Sylvain Oudeyer
Dr. Jean-François Brière
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. Catalysts 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 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

  • organocatalysis
  • asymmetric synthesis
  • enantioselective transformation
  • heterocycles
  • chiral compounds

Published Papers (2 papers)

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Research

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21 pages, 3191 KiB  
Article
Heteroaromatic N-Oxides Modified with a Chiral Oxazoline Moiety, Synthesis and Catalytic Applications
by Zuzanna Wrzeszcz and Renata Siedlecka
Catalysts 2021, 11(4), 444; https://0-doi-org.brum.beds.ac.uk/10.3390/catal11040444 - 30 Mar 2021
Cited by 2 | Viewed by 4136
Abstract
Interesting properties of N-oxides and pyridine oxazoline compounds have become the starting point to synthesize compounds connecting both groups. A multi-step synthesis of a series of chiral oxazoline substituted pyridine N-oxides, alkyl derived of pyridine N-oxides, bipyridine N-oxides, and isoquinoline N-oxides, based on [...] Read more.
Interesting properties of N-oxides and pyridine oxazoline compounds have become the starting point to synthesize compounds connecting both groups. A multi-step synthesis of a series of chiral oxazoline substituted pyridine N-oxides, alkyl derived of pyridine N-oxides, bipyridine N-oxides, and isoquinoline N-oxides, based on amino alcohols derived from natural amino acids or other previously prepared, is presented herein. Various synthetic pathways have been designed and tested according to the properties and limitations imposed by the target products. The encountered problems related to the stability of the products were discussed. The resulting compounds (eighteen structures) were tested as catalysts in th e allylation of benzaldehyde (obtaining up to 79% ee) as well as in nitroaldol reaction (obtaining up to 48% ee). Full article
(This article belongs to the Special Issue Organocatalytic Asymmetric Synthesis or Transformation of Heterocycles)
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Review

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37 pages, 19142 KiB  
Review
Organocatalysis: A Tool of Choice for the Enantioselective Nucleophilic Dearomatization of Electron-Deficient Six-Membered Ring Azaarenium Salts
by Claire Segovia, Pierre-Antoine Nocquet, Vincent Levacher, Jean-François Brière and Sylvain Oudeyer
Catalysts 2021, 11(10), 1249; https://0-doi-org.brum.beds.ac.uk/10.3390/catal11101249 - 18 Oct 2021
Cited by 6 | Viewed by 3143
Abstract
Nucleophilic dearomatization of azaarenium salts is a powerful strategy to access 3D scaffolds of interest from easily accessible planar aromatic azaarene compounds. Moreover, this approach yields complex dihydroazaarenes by allowing the functionalization of the scaffold simultaneously to the dearomatization step. On the other [...] Read more.
Nucleophilic dearomatization of azaarenium salts is a powerful strategy to access 3D scaffolds of interest from easily accessible planar aromatic azaarene compounds. Moreover, this approach yields complex dihydroazaarenes by allowing the functionalization of the scaffold simultaneously to the dearomatization step. On the other side, organocatalysis is nowadays recognized as one of the pillars of the asymmetric catalysis field of research and is well-known to afford a high level of enantioselectivity for a myriad of transformations thanks to well-organized transition states resulting from low-energy interactions (electrostatic and/or H-bonding interactions…). Consequently, in the last fifteen years, organocatalysis has met great success in nucleophilic dearomatization of azaarenium salts. This review summarizes the work achieved up to date in the field of organocatalyzed nucleophilic dearomatization of azaarenium salts (mainly pyridinium, quinolinium, quinolinium and acridinium salts). A classification by organocatalytic mode of activation will be disclosed by shedding light on their related advantages and drawbacks. The versatility of the dearomatization approach will also be demonstrated by discussing several chemical transformations of the resulting dihydroazaarenes towards the synthesis of structurally complex compounds. Full article
(This article belongs to the Special Issue Organocatalytic Asymmetric Synthesis or Transformation of Heterocycles)
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