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Catalysts
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Asymmetric Catalysis in Organic Synthesis
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Asymmetric Catalysis in Organic Synthesis

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalytic Materials".

Deadline for manuscript submissions: closed (31 December 2018) | Viewed by 28867

Special Issue Editors

Prof. Dr. Ashraf Ghanem

E-Mail Website
Guest Editor
Chirality Group, Biomedical Science Program, School of Science, Faculty of Science and Technology, University of Canberra, Canberra, ACT 2601, Australia
Interests: chirality; enantioselective nano chromatography; asymmetric catalysis; chiral analysis
Special Issues, Collections and Topics in MDPI journals
Dr. Frady Gouany

E-Mail Website
Guest Editor
Biomedical Science Department, Faculty of ESTeM, Room 27B18, University of Canberra, Canberra, Bruce, ACT 2601, Australia
Interests: asymmetric synthesis; enantioselective catalysis; metal-carbene chemistry; chiral analysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Asymmetric catalysis (also known as enantioselective catalysis) is considered as one of the ultimate solutions for gaining access to enantiomerically enriched/pure compounds, in which a metal complex carrying chiral ligands has its own merits to return many equivalents of the desired enantiomerically-enriched chiral product. Due to the increasing number of available methodologies to access enantiomerically-enriched/pure organic compounds, the scope of asymmetric catalysis has greatly expanded to include a broad range of chemical transformations. Ideally, a practical asymmetric catalyst should provide high yield and selectivity (chemo-, diastereo- and enantioselectivity) for a broad range of substrates in different reaction conditions, whilst being inexpensive and readily available in both enantiopure forms. A large number of complexes have been already reported, and many of these complexes have been studied and used in asymmetric catalysis.

This Special Issue aims to cover recent progress and advances in the field of asymmetric catalysis. This includes, but is not restricted to, the design and synthesis of novel chiral catalysts, their applications in the development of new asymmetric methodologies, and in the synthesis of commercially-valuable molecules and natural products.

Prof. Dr. Ashraf Ghanem
Dr. Frady Gouany
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 2200 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

  • Asymmetric Synthesis
  • Chiral Ligands
  • Chiral Catalysts
  • Enantiomeric Excess
  • Enantioselectivity

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Published Papers (6 papers)

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Editorial

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2 pages, 167 KiB  
Editorial
Asymmetric Catalysis in Organic Synthesis
by Frady G. Adly and Ashraf Ghanem
Catalysts 2019, 9(9), 775; https://doi.org/10.3390/catal9090775 - 15 Sep 2019
Cited by 3 | Viewed by 3676
Abstract
Biological systems, in most cases, recognize a pair of enantiomers as different substances eliciting different responses [...] Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)

Research

Jump to: Editorial, Review

22 pages, 1421 KiB  
Article
NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center
by Zbigniew Rafiński
Catalysts 2019, 9(2), 192; https://doi.org/10.3390/catal9020192 - 20 Feb 2019
Cited by 8 | Viewed by 3715
Abstract
A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived [...] Read more.
A highly efficient and enantioselective approach to the synthesis of functionalized benzofuran-3(2H)-ones is presented. It proceeds via an intramolecular Stetter reaction using β,β-disubstituted Michael acceptors in the construction of five-membered rings with fully-substituted quaternary stereogenic centers and is promoted by terpene-derived triazolium salts. As a result, a series of chiral 2,2-disubstituted benzofuran-3(2H)-one derivatives with linear, branched, and cyclic aliphatic substitutions on the quaternary stereogenic center were obtained in high yields and with excellent enantioselectivities of up to 99% ee. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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15 pages, 3687 KiB  
Article
Theoretical Calculations on the Mechanism of Enantioselective Copper(I)-Catalyzed Addition of Enynes to Ketones
by Hanwei Li, Mingliang Luo, Guohong Tao and Song Qin
Catalysts 2018, 8(9), 359; https://doi.org/10.3390/catal8090359 - 28 Aug 2018
Cited by 7 | Viewed by 4096
Abstract
Computational investigations on the bisphospholanoethane (BPE)-ligated Cu-catalyzed enantioselective addition of enynes to ketones were performed with the density functional theory (DFT) method. Two BPE-mesitylcopper (CuMes) catalysts, BPE-CuMes and (S,S)-Ph-BPE–CuMes, were employed to probe the reaction mechanism with the emphasis on stereoselectivity. [...] Read more.
Computational investigations on the bisphospholanoethane (BPE)-ligated Cu-catalyzed enantioselective addition of enynes to ketones were performed with the density functional theory (DFT) method. Two BPE-mesitylcopper (CuMes) catalysts, BPE-CuMes and (S,S)-Ph-BPE–CuMes, were employed to probe the reaction mechanism with the emphasis on stereoselectivity. The calculations on the BPE-CuMes system indicate that the active metallized enyne intermediate acts as the catalyst for the catalytic cycle. The catalytic cycle involves two steps: (1) ketone addition to the alkene moiety of the metallized enyne; and (2) metallization of the enyne followed by the release of product with the recovery of the active metallized enyne intermediate. The first step accounts for the distribution of the products, and therefore is the stereo-controlling step in chiral systems. In the chiral (S,S)-Ph-BPE–CuMes system, the steric hindrance is vital for the distribution of products and responsible for the stereoselectivity of this reaction. The steric hindrance between the phenyl ring of the two substrates and groups at the chiral centers in the ligand skeleton is identified as the original of the stereoselectivity for the titled reaction. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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Graphical abstract

15 pages, 2549 KiB  
Article
Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity
by Frady G. Adly, Hannah Bollard, Michael G. Gardiner and Ashraf Ghanem
Catalysts 2018, 8(7), 268; https://doi.org/10.3390/catal8070268 - 30 Jun 2018
Cited by 5 | Viewed by 4906
Abstract
The current report contributes to the understanding of the stereoselectivity of chiral dirhodium(II) carboxylate catalysts carrying N-protected tert-leucine ligands. Investigating the possible effect of ligand stereo-purity on catalyst structure and enantioselectivity was carried out. This was justified through a new X-ray [...] Read more.
The current report contributes to the understanding of the stereoselectivity of chiral dirhodium(II) carboxylate catalysts carrying N-protected tert-leucine ligands. Investigating the possible effect of ligand stereo-purity on catalyst structure and enantioselectivity was carried out. This was justified through a new X-ray crystal structure for Rh2(S,S,S,R-PTTL)4 diastereomer. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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9 pages, 906 KiB  
Communication
Synthesis of New C2-Symmetric Six-Membered NHCs and Their Application for the Asymmetric Diethylzinc Addition of Arylaldehydes
by Jie Li, Bihui Zhou, Yajie Jiang and Xiaoming Liu
Catalysts 2018, 8(2), 46; https://doi.org/10.3390/catal8020046 - 26 Jan 2018
Cited by 6 | Viewed by 3370
Abstract
A concise method for the preparation of new 3,4,5,6-tetrahydropyrimidinium salts was presented in this paper. Further application of these salts in asymmetric diethylzinc addition of arylaldehydes was explored, giving the corresponding chiral second alcohols in good yields and moderate enantioselectivities. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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Review

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4126 KiB  
Review
On the Structure of Chiral Dirhodium(II) Carboxylate Catalysts: Stereoselectivity Relevance and Insights
by Frady G. Adly
Catalysts 2017, 7(11), 347; https://doi.org/10.3390/catal7110347 - 20 Nov 2017
Cited by 32 | Viewed by 6710
Abstract
Modern experiments have offered alternative interpretations on the symmetry of chiral dirhodium(II) carboxylate complexes and its relationship to their level of enantioselectivity. So, this contribution is to provide an insight on how the knowledge around the structure of these catalysts has evolved with [...] Read more.
Modern experiments have offered alternative interpretations on the symmetry of chiral dirhodium(II) carboxylate complexes and its relationship to their level of enantioselectivity. So, this contribution is to provide an insight on how the knowledge around the structure of these catalysts has evolved with a particular emphasis on the impact of this knowledge on enantioselectivity prediction and catalyst design. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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