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Catalysts
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Catalytic Asymmetric Epoxidation: Recent Progress
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Catalytic Asymmetric Epoxidation: Recent Progress

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 (20 October 2021) | Viewed by 30646

Special Issue Editor

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
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Special Issue Information

Dear Colleagues,

Epoxides (oxiranes) constitute an important class of compounds both in biology and chemistry. The epoxide functionality is found in many natural products of diverse biological properties, in pharmaceutical molecules and in synthetic intermediates towards the synthesis of more complex compounds which support a range of applications such as medicine, polymers and other high-performance materials. Over the past decades, the synthesis and further exploitation of epoxides has been the subject of intense research efforts and significant advances have been made across all fronts of their chemistry and biology and uses thereof. Several reviews and book chapters have been dedicated to specific aspects of the epoxide field; yet, significant developments continue to emerge, rendering the epoxide moiety a special theme that continues to attract substantial interest. It is therefore warranted that the most recent developments in the epoxide field be captured and communicated in a concise and holistic manner. This Special Issue intends to serve this purpose and constitute a point of reference with respect to: (a) natural occurrence, properties, and reactivity of epoxides; (b) epoxidation methods (direct/indirect, stoichiometric/catalysed, regio-, distrereo- and enantioselective); and (c) applications and future prospects in research and industry.

Dr. Gerasimos Rassias
Guest Editor

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Published Papers (2 papers)

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Research

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9 pages, 1920 KiB  
Article
Manganese Catalysts with Tetradentate N-donor Pyridine-Appended Bipiperidine Ligands for Olefin Epoxidation Reactions: Ligand Electronic Effect and Mechanism
by Fengfan Zhu, Guang Yang, Adam J. Zoll, Elena V. Rybak-Akimova and Xinbao Zhu
Catalysts 2020, 10(3), 285; https://doi.org/10.3390/catal10030285 - 2 Mar 2020
Cited by 9 | Viewed by 4268
Abstract
In this work, we described an electron-rich manganese mesoPYBP catalyst, Mn-SR-mesoPYBP(ClO4)2, by introducing electron-donating substituents on the mesoPYBP ligand. We optimized the catalytic performance in olefin epoxidation with H2O2 in the presence [...] Read more.
In this work, we described an electron-rich manganese mesoPYBP catalyst, Mn-SR-mesoPYBP(ClO4)2, by introducing electron-donating substituents on the mesoPYBP ligand. We optimized the catalytic performance in olefin epoxidation with H2O2 in the presence of acetic acid. The electron paramagnetic resonance (EPR) and cyclic voltammetry (CV) studies supported that an electronic effect could stabilize the high-valent intermediates in the catalytic cycles of the catalyst, which largely improved the catalytic performance and the reactivity of olefin epoxidation. Full article
(This article belongs to the Special Issue Catalytic Asymmetric Epoxidation: Recent Progress)
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Review

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65 pages, 11791 KiB  
Review
Epoxide Syntheses and Ring-Opening Reactions in Drug Development
by Fotini Moschona, Ioanna Savvopoulou, Maria Tsitopoulou, Despoina Tataraki and Gerasimos Rassias
Catalysts 2020, 10(10), 1117; https://doi.org/10.3390/catal10101117 - 27 Sep 2020
Cited by 91 | Viewed by 25461
Abstract
This review concentrates on success stories from the synthesis of approved medicines and drug candidates using epoxide chemistry in the development of robust and efficient syntheses at large scale. The focus is on those parts of each synthesis related to the substrate-controlled/diastereoselective and [...] Read more.
This review concentrates on success stories from the synthesis of approved medicines and drug candidates using epoxide chemistry in the development of robust and efficient syntheses at large scale. The focus is on those parts of each synthesis related to the substrate-controlled/diastereoselective and catalytic asymmetric synthesis of epoxide intermediates and their subsequent ring-opening reactions with various nucleophiles. These are described in the form of case studies of high profile pharmaceuticals spanning a diverse range of indications and molecular scaffolds such as heterocycles, terpenes, steroids, peptidomimetics, alkaloids and main stream small molecules. Representative examples include, but are not limited to the antihypertensive diltiazem, the antidepressant reboxetine, the HIV protease inhibitors atazanavir and indinavir, efinaconazole and related triazole antifungals, tasimelteon for sleep disorders, the anticancer agent carfilzomib, the anticoagulant rivaroxaban the antibiotic linezolid and the antiviral oseltamivir. Emphasis is given on aspects of catalytic asymmetric epoxidation employing metals with chiral ligands particularly with the Sharpless and Jacobsen–Katsuki methods as well as organocatalysts such as the chiral ketones of Shi and Yang, Pages’s chiral iminium salts and typical chiral phase transfer agents. Full article
(This article belongs to the Special Issue Catalytic Asymmetric Epoxidation: Recent Progress)
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