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Catalysts
Special Issues
Advances in Asymmetric Organocatalytic Reactions
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Advances in Asymmetric Organocatalytic Reactions

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 November 2022) | Viewed by 7745

Special Issue Editors

Dr. Wioleta Cieslik

E-Mail Website
Guest Editor
Institute of Chemistry, University of Silesia, 75. Pułku Piechoty 1, 41-500 Chorzów, Poland
Interests: organocatalysis; asymmetric synthesis; cycloaddition; nanomaterials; anticancer activity; kinase inhibition; antifungal activity
Dr. Rosaria Schettini

E-Mail Website
Guest Editor
Department of Chemistry and Biology, University of Salerno, 84084 Salerno, Italy
Interests: synthesis of cyclic peptoids and their derivatives; phase-transfer catalysts; asymmetric synthesis; macrocyclic catalysts
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Asymmetric organocatalysis has recently experienced impressive growth and is considered to be an independent set of synthetic tools for the preparation of chiral organic molecules. Due to the numerous advantages of organocatalysis, including high efficiency and stereoselectivity of reactions, it has quickly found applications in synthetic, medicinal, and materials chemistry.

Organocatalysts are metal free, non-toxic, and environmentally benign. In addition, they are durable compounds and many of them are commercially available or are easily synthesized. They are usually stable under aerobic conditions and their reactions do not require extremely dry conditions. Frequently, their reactions are carried out under mild conditions and at high concentrations, thereby avoiding the use of large amounts of solvents and minimizing the amount of waste. In addition to these features, organocatalysts are tolerant of many functional groups and thus do not require any time-consuming manipulation of protective groups.

This Special Issue will provide a contemporary overview of progress in the broad field of asymmetric organocatalysis. Topics include the design and synthesis of organocatalysts, the development of new catalytic systems, applications of organocatalysts in asymmetric synthesis, mechanistic studies, and synthetic applications in the preparation of chiral products important in the pharmaceutical or material sciences. Full papers, communications, and mini-reviews are welcome in this issue.

Dr. Wioleta Cieslik
Dr. Rosaria Schettini
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
  • enantioselectivity
  • diastereoisomers
  • enantiomers
  • bifunctional catalysis
  • catalyst immobilization
  • nonmetal catalysis
  • photocatalysis
  • chirality

Published Papers (4 papers)

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Research

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16 pages, 17517 KiB  
Article
Diastereo- and Enantioselective Synthesis of Highly Functionalized Tetrahydropyridines by Recyclable Novel Bifunctional C2-Symmetric Ionic Liquid–Supported (S)-Proline Organocatalyst
by Prabhakara Madivalappa Davanagere, Mrinmoy De, Kaushik Chanda and Barnali Maiti
Catalysts 2023, 13(1), 209; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13010209 - 16 Jan 2023
Cited by 4 | Viewed by 1650
Abstract
An efficient, novel bifunctional C2-symmetric ionic liquid–supported (S)-proline organocatalyst 7 was developed for a one-pot, five-component reaction involving β-keto esters 8, aryl aldehydes 9, and aryl amines 10, affording highly functionalized tetrahydropyridines 11a–o by simultaneous [...] Read more.
An efficient, novel bifunctional C2-symmetric ionic liquid–supported (S)-proline organocatalyst 7 was developed for a one-pot, five-component reaction involving β-keto esters 8, aryl aldehydes 9, and aryl amines 10, affording highly functionalized tetrahydropyridines 11a–o by simultaneous generation of fives bonds and two stereogenic centers with extraordinary diastereo- and enantioselectivities (up to >99:1 dr, 95:5 er) in isopropanol with high yields (up to 92%). This protocol provides quick access to diverse enantio-enriched, highly functionalized diastereo- and enantioselective tetrahydropyridines in a green medium without any column chromatographic purification. The catalyst was recycled five times without significant loss of its catalytic activity. Full article
(This article belongs to the Special Issue Advances in Asymmetric Organocatalytic Reactions)
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8 pages, 1181 KiB  
Article
Highly Efficient Asymmetric Morita–Baylis–Hillman Reaction Promoted by Chiral Aziridine-Phosphines
by Aleksandra Buchcic-Szychowska, Anna Zawisza, Stanisław Leśniak and Michał Rachwalski
Catalysts 2022, 12(4), 394; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12040394 - 31 Mar 2022
Cited by 3 | Viewed by 1747
Abstract
Continuing our research on the use of organophosphorus derivatives of aziridines in asymmetric synthesis and expanding the scope of their applicability, chiral aziridine-phosphines obtained earlier in our laboratory were used as chiral catalysts in the asymmetric Morita–Baylis–Hillman reaction of methyl vinyl ketone and [...] Read more.
Continuing our research on the use of organophosphorus derivatives of aziridines in asymmetric synthesis and expanding the scope of their applicability, chiral aziridine-phosphines obtained earlier in our laboratory were used as chiral catalysts in the asymmetric Morita–Baylis–Hillman reaction of methyl vinyl ketone and methyl acrylate with various aromatic aldehydes. The desired chiral products were formed in moderate to high chemical yields and with enantiomeric excess reaching value of 98% ee in some cases. The use of catalysts being pairs of enantiomers led to the desired products with opposite absolute configurations. Full article
(This article belongs to the Special Issue Advances in Asymmetric Organocatalytic Reactions)
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Review

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20 pages, 6257 KiB  
Review
Peptidomimetic-Based Asymmetric Catalysts
by Ibrahim Khettar, Alicja Malgorzata Araszczuk and Rosaria Schettini
Catalysts 2023, 13(2), 244; https://0-doi-org.brum.beds.ac.uk/10.3390/catal13020244 - 21 Jan 2023
Viewed by 1765
Abstract
Despite the great advantages of peptidomimetic scaffolds, there are only a few examples of their application in the field of asymmetric catalysis. Peptidomimetic scaffolds offer numerous advantages related to their easy preparation, modular and tunable structures, and biomimetic features, which make them well [...] Read more.
Despite the great advantages of peptidomimetic scaffolds, there are only a few examples of their application in the field of asymmetric catalysis. Peptidomimetic scaffolds offer numerous advantages related to their easy preparation, modular and tunable structures, and biomimetic features, which make them well suited as chiral catalysts. This review underlines the structure–function relationship for catalytic properties towards efficient enantioselective catalysis. Full article
(This article belongs to the Special Issue Advances in Asymmetric Organocatalytic Reactions)
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32 pages, 18259 KiB  
Review
Catalytic Efficiency of Primary α-Amino Amides as Multifunctional Organocatalysts in Recent Asymmetric Organic Transformations
by Ummareddy Venkata Subba Reddy, Bheemreddy Anusha, Zubeda Begum, Chigusa Seki, Yuko Okuyama, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita and Hiroto Nakano
Catalysts 2022, 12(12), 1674; https://0-doi-org.brum.beds.ac.uk/10.3390/catal12121674 - 19 Dec 2022
Cited by 4 | Viewed by 1896
Abstract
Chiral primary α-amino amides, consisting of an adjacent enamine bonding site (Bronsted base site), a hydrogen bonding site (Bronsted acid site), and flexible bulky substituent groups to modify the steric factor, are proving to be extremely valuable bifunctional organocatalysts for a wide range [...] Read more.
Chiral primary α-amino amides, consisting of an adjacent enamine bonding site (Bronsted base site), a hydrogen bonding site (Bronsted acid site), and flexible bulky substituent groups to modify the steric factor, are proving to be extremely valuable bifunctional organocatalysts for a wide range of asymmetric organic transformations. Primary α-amino amides are less expensive alternatives to other primary amino organocatalysts, such as chiral diamines and cinchona-alkaloid-derived primary amines, as they are easy to synthesize, air-stable, and allow for the incorporation of a variety of functional groups. In recent years, we have demonstrated the catalytic use of simple primary α-amino amides and their derivatives as organocatalysts for the aldol reaction, Strecker reaction, Michael tandem reaction, allylation of aldehydes, reduction of N-Aryl mines, opening of epoxides, hydrosilylation, asymmetric hydrogen transfer, and N-specific nitrosobenzene reaction with aldehydes. Full article
(This article belongs to the Special Issue Advances in Asymmetric Organocatalytic Reactions)
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