New Trends in Asymmetric Catalysis

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 (31 August 2020) | Viewed by 45655

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Dipartimento di Chimica e Biologia "Adolfo Zambelli" DCB, Università di Salerno, Salerno, Italy
Interests: stereoselective organocatalyzed and metal-catalyzed reactions; enantioselective synthesis; phase–transfer catalysis; macrocyclic catalysts; synthesis and applications of cyclic peptoids
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Guest Editor
Dipartimento di Chimica e Biologia "Adolfo Zambelli" DCB, Università di Salerno, Salerno, Italy
Interests: synthesis of cyclic peptoids and their derivatives; phase-transfer catalysts; asymmetric synthesis; macrocyclic catalysts; biological applications; MRI contrast agents
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The ever-increasing demand of enantiopure or enantioenriched chiral molecules in diverse industrial sectors, such as the pharmaceutical, agrochemical, cosmetic, food chemistry and material science, has determined the flourishing of asymmetric synthesis throughout the past half century. In this respect, asymmetric catalysis is widely recognized as the ideal strategy for enantioselective synthesis, since, as a matter of principle, only a small amount of nonracemic chiral catalysts is generally needed to yield a large amount of nonracemic chiral product, resulting in a convenient multiplication of chirality. This concept has economic implications that make it especially appealing for industrial applications. On this basis, asymmetric catalysis, which is founded on three main pillars—metal-catalysis, organocatalysis, and biocatalysis—has grown explosively during the last few decades, and continual developments can be witnessed in this active research area. An impressive number of enantioselective transformations and efficient catalysts have been reported to date. Despite this, most of the them are amenable to improvement, especially for industrial applications. Current efforts are devoted to the rational design of novel chiral catalyst architectures in order to improve the enantioselectivity of known processes, as well as to expand the scope of asymmetric transformations. In addition, other criteria should be considered, such as product selectivity, turnover number and frequency, availability and cost of precursors, ease of preparation, environmental impact, and the possibility of recycling.

This Special Issue aims to cover recent advances in various aspects of asymmetric catalysis, including design and application of novel catalysts (metal compounds, organocatalysts, peptide derivatives, phase-transfer agents), mechanistic studies of enantioselective processes, innovative organic transformations, and others. Research articles, short communications, brief reports, and review papers on this topic are welcomed.

Dr. Giorgio Della Sala
Dr. Rosaria Schettini
Guest Editors

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Keywords

  • Chiral catalysts 
  • Chiral ligands
  • Enantioselectivity
  • Asymmetric organocatalysis 
  • Enantioselective industrial processes 
  • Asymmetric metal catalysis
  • Asymmetric phase–transfer catalysis
  • Enantioselective enzyme-catalyzed reactions 
  • Kinetic resolution 
  • Supported chiral catalysts

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Published Papers (6 papers)

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Editorial

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3 pages, 169 KiB  
Editorial
New Trends in Asymmetric Catalysis
by Rosaria Schettini and Giorgio Della Sala
Catalysts 2021, 11(3), 306; https://doi.org/10.3390/catal11030306 - 26 Feb 2021
Cited by 2 | Viewed by 2006
Abstract
As far back as the mid-nineteenth century, the studies of Louis Pasteur brought to light the essential role of molecular chirality in biology [...] Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)

Research

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22 pages, 1040 KiB  
Article
A Simple and Efficient Protocol for Proline-Catalysed Asymmetric Aldol Reaction
by Marco Giuseppe Emma, Alice Tamburrini, Ada Martinelli, Marco Lombardo, Arianna Quintavalla and Claudio Trombini
Catalysts 2020, 10(6), 649; https://doi.org/10.3390/catal10060649 - 10 Jun 2020
Cited by 15 | Viewed by 7483
Abstract
The proline-catalysed asymmetric aldol reaction is usually carried out in highly dipolar aprotic solvents (dimethylsulfoxide, dimethylformamide, acetonitrile) where proline presents an acceptable solubility. Protic solvents are generally characterized by poor stereocontrol (e.g., methanol) or poor reactivity (e.g., water). Here, we report that water/methanol [...] Read more.
The proline-catalysed asymmetric aldol reaction is usually carried out in highly dipolar aprotic solvents (dimethylsulfoxide, dimethylformamide, acetonitrile) where proline presents an acceptable solubility. Protic solvents are generally characterized by poor stereocontrol (e.g., methanol) or poor reactivity (e.g., water). Here, we report that water/methanol mixtures are exceptionally simple and effective reaction media for the intermolecular organocatalytic aldol reaction using the simple proline as the catalyst. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)
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Review

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24 pages, 8445 KiB  
Review
Recent Advances in Asymmetric Catalytic Electrosynthesis
by Cristiana Margarita and Helena Lundberg
Catalysts 2020, 10(9), 982; https://doi.org/10.3390/catal10090982 - 01 Sep 2020
Cited by 27 | Viewed by 7690
Abstract
The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus [...] Read more.
The renewed interest in electrosynthesis demonstrated by organic chemists in the last years has allowed for rapid development of new methodologies. In this review, advances in enantioselective electrosynthesis that rely on catalytic amounts of organic or metal-based chiral mediators are highlighted with focus on the most recent developments up to July 2020. Examples of C-H functionalization, alkene functionalization, carboxylation and cross-electrophile couplings are discussed, along with their related mechanistic aspects. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)
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65 pages, 41369 KiB  
Review
Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes
by Anna Lidskog, Yutang Li and Kenneth Wärnmark
Catalysts 2020, 10(6), 705; https://doi.org/10.3390/catal10060705 - 23 Jun 2020
Cited by 19 | Viewed by 8408
Abstract
The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the [...] Read more.
The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)
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22 pages, 5867 KiB  
Review
α-Functionalization of Imines via Visible Light Photoredox Catalysis
by Alberto F. Garrido-Castro, M. Carmen Maestro and José Alemán
Catalysts 2020, 10(5), 562; https://doi.org/10.3390/catal10050562 - 19 May 2020
Cited by 49 | Viewed by 12556
Abstract
The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel [...] Read more.
The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)
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23 pages, 9467 KiB  
Review
The Combination of Lewis Acid with N-Heterocyclic Carbene (NHC) Catalysis
by Qianfa Jia, Yaqiong Li, Yinhe Lin and Qiao Ren
Catalysts 2019, 9(10), 863; https://doi.org/10.3390/catal9100863 - 16 Oct 2019
Cited by 12 | Viewed by 5734
Abstract
In the last ten years, the combination of Lewis acid with N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in a variety of important asymmetric synthesis, due to the ready availability of starting materials, operational simplicity and mild reaction conditions. [...] Read more.
In the last ten years, the combination of Lewis acid with N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in a variety of important asymmetric synthesis, due to the ready availability of starting materials, operational simplicity and mild reaction conditions. Recent findings illustrate that Lewis acid could largely enhance the efficiency and enantioselectivity, reverse the diastereoselectivity, and even influence the pathway of the same reaction partners. Herein, this review aims to reveal the recent advances in NHC-Lewis acid synergistically promoted enantioselective reactions for the expeditious assembly of versatile biologically important chiral pharmaceuticals and natural products. Full article
(This article belongs to the Special Issue New Trends in Asymmetric Catalysis)
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