Asymmetric Catalysis

A special issue of Symmetry (ISSN 2073-8994).

Deadline for manuscript submissions: closed (30 November 2015) | Viewed by 53069

Special Issue Editor


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Guest Editor
Institut für Organische Chemie I, Friedrich-Alexander Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
Interests: asymmetric organocatalysis and organo-autocatalysis; synthesis of natural product hybrids for medicinal chemistry; redox-active metal complexes for asymmetric oxidation reactions
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Special Issue Information

Dear Colleagues,

Symmetry invites manuscripts for the Special Issue on Asymmetric Catalysis, a field of central importance for the production of enantiomerically pure chiral drugs, natural products, and important molecules for materials chemistry. This issue is devoted to the recent aspects of asymmetric organo- and metal-catalysis, combination of organocatalysis with metal- and/or bio-catalysis.
Both original research papers and reviews dealing with the design, synthesis and use of new enantioselective catalytic systems that promote the formation of versatile chiral building-blocks, fine chemicals, pharmaceuticals, flavors, biologically active molecules, and materials will be considered.

Prof. Dr. Svetlana Tsogoeva
Guest Editor

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Keywords

  • organocatalysis,
  • metal catalysis,
  • enantioselectivity,
  • fine chemicals,
  • bioactive compounds

Published Papers (7 papers)

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Research

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10117 KiB  
Article
Organocatalytic Asymmetric α-Chlorination of 1,3-Dicarbonyl Compounds Catalyzed by 2-Aminobenzimidazole Derivatives
by Daniel Serrano Sánchez, Alejandro Baeza and Diego A. Alonso
Symmetry 2016, 8(1), 3; https://doi.org/10.3390/sym8010003 - 13 Jan 2016
Cited by 11 | Viewed by 6422
Abstract
Bifunctional chiral 2-aminobenzimidazole derivatives 1 and 2 catalyze the enantioselective stereodivergent α-chlorination of β-ketoesters and 1,3-diketone derivatives with up to 50% ee using N-chlorosuccinimide (NCS) or 2,3,4,4,5,6-hexachloro-2,5-cyclohexadien-1-one as electrophilic chlorine sources. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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1345 KiB  
Article
Natural Abundance Isotopic Chirality in the Reagents of the Soai Reaction
by Béla Barabás, Róbert Kurdi and Gyula Pályi
Symmetry 2016, 8(1), 2; https://doi.org/10.3390/sym8010002 - 8 Jan 2016
Cited by 13 | Viewed by 5428
Abstract
Isotopic chirality influences sensitively the enantiomeric outcome of the Soai asymmetric autocatalysis. Therefore magnitude and eventual effects of isotopic chirality caused by natural abundance isotopic substitution (H, C, O, Zn) in the reagents of the Soai reaction were analyzed by combinatorics and probability [...] Read more.
Isotopic chirality influences sensitively the enantiomeric outcome of the Soai asymmetric autocatalysis. Therefore magnitude and eventual effects of isotopic chirality caused by natural abundance isotopic substitution (H, C, O, Zn) in the reagents of the Soai reaction were analyzed by combinatorics and probability calculations. Expectable enantiomeric excesses were calculated by the Pars–Mills equation. It has been found that the chiral isotopic species formed by substitution in the otherwise achiral reagents provide enantiomeric excess (e.e.) levels that are higher than the sensitivity threshold of the Soai autocatalysis towards chiral induction. Consequently, possible chiral induction exerted by these e.e. values should be taken into account in considerations regarding the molecular events and the mechanism of the chiral induction in the Soai reaction. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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674 KiB  
Article
Enantioselective Organocatalysis in Microreactors: Continuous Flow Synthesis of a (S)-Pregabalin Precursor and (S)-Warfarin
by Riccardo Porta, Maurizio Benaglia, Francesca Coccia, Sergio Rossi and Alessandra Puglisi
Symmetry 2015, 7(3), 1395-1409; https://doi.org/10.3390/sym7031395 - 4 Aug 2015
Cited by 35 | Viewed by 8668
Abstract
Continuous flow processes have recently emerged as a powerful technology for performing chemical transformations since they ensure some advantages over traditional batch procedures. In this work, the use of commercially available and affordable PEEK (Polyetheretherketone) and PTFE (Polytetrafluoroethylene) HPLC (High Performance Liquid Chromatography) [...] Read more.
Continuous flow processes have recently emerged as a powerful technology for performing chemical transformations since they ensure some advantages over traditional batch procedures. In this work, the use of commercially available and affordable PEEK (Polyetheretherketone) and PTFE (Polytetrafluoroethylene) HPLC (High Performance Liquid Chromatography) tubing as microreactors was exploited to perform organic reactions under continuous flow conditions, as an alternative to the commercial traditional glass microreactors. The wide availability of tubing with different sizes allowed quickly running small-scale preliminary screenings, in order to optimize the reaction parameters, and then to realize under the best experimental conditions a reaction scale up for preparative purposes. The gram production of some Active Pharmaceutical Ingredients (APIs) such as (S)-Pregabalin and (S)-Warfarin was accomplished in short reaction time with high enantioselectivity, in an experimentally very simple procedure. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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705 KiB  
Article
Development of Guanidine-Bisurea Bifunctional Organocatalyst Bearing Chirality at the Inner and Outer Sides of the Urea Groups, and Application to Enantioselective α-Hydroxylation of Pyranoindolizine Intermediate for Camptothecin Synthesis
by Minami Odagi, Tatsuya Watanabe and Kazuo Nagasawa
Symmetry 2015, 7(1), 43-52; https://doi.org/10.3390/sym7010043 - 14 Jan 2015
Cited by 3 | Viewed by 5444
Abstract
Pyranoindolizine is a tricyclic structure found in various biologically active compounds, such as camptothecin (CPT) and its derivatives. In the case of CPTs, the chirality at the α-position in the α-hydroxyl lactone moiety of pyranoindolizine is important for the antitumor activity. This paper [...] Read more.
Pyranoindolizine is a tricyclic structure found in various biologically active compounds, such as camptothecin (CPT) and its derivatives. In the case of CPTs, the chirality at the α-position in the α-hydroxyl lactone moiety of pyranoindolizine is important for the antitumor activity. This paper deals with enantioselective oxidation of the α-position in pyranoindolizine lactone, which corresponds at C20 in CPT, with cumene hydroperoxide (CHP) in the presence of newly synthesized guanidine-bisurea bifunctional organocatalysts bearing chirality on both the inner and outer sides of the urea groups. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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Review

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1810 KiB  
Review
Synthesis of Chiral Cyclic Carbonates via Kinetic Resolution of Racemic Epoxides and Carbon Dioxide
by Xiao Wu, José A. Castro-Osma and Michael North
Symmetry 2016, 8(1), 4; https://doi.org/10.3390/sym8010004 - 14 Jan 2016
Cited by 23 | Viewed by 8505
Abstract
The catalytic synthesis of cyclic carbonates using carbon dioxide as a C1-building block is a highly active area of research. Here, we review the catalytic production of enantiomerically enriched cyclic carbonates via kinetic resolution of racemic epoxides catalysed by metal-containing catalyst systems. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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8867 KiB  
Review
Cyclodextrins in Asymmetric and Stereospecific Synthesis
by Fliur Macaev and Veaceslav Boldescu
Symmetry 2015, 7(4), 1699-1720; https://doi.org/10.3390/sym7041699 - 24 Sep 2015
Cited by 29 | Viewed by 8740
Abstract
Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their [...] Read more.
Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their division into three main groups: (1) cyclodextrins promoting asymmetric and stereospecific catalysis in water; (2) cyclodextrins’ complexes with transition metals as asymmetric and stereospecific catalysts; and (3) cyclodextrins’ non-metallic derivatives as asymmetric and stereospecific catalysts. The scope of this review is to systematize existing information on the contribution of cyclodextrins to asymmetric and stereospecific synthesis and, thus, to facilitate further development in this direction. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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922 KiB  
Review
Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives
by Isaac G. Sonsona, Eugenia Marqués-López and Raquel P. Herrera
Symmetry 2015, 7(3), 1519-1535; https://doi.org/10.3390/sym7031519 - 26 Aug 2015
Cited by 34 | Viewed by 8872
Abstract
The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis [...] Read more.
The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds. This review covers the particular case of the asymmetric synthesis of 2-amino-3-cyano-4H-chromenes using organocatalysis. Herein, we show the most illustrative examples of the methods developed by diverse research groups, following a classification based on these five different approaches: (1) addition of naphthol compounds to substituted α,α-dicyanoolefins; (2) addition of malononitrile to substituted o-vinylphenols; (3) addition of malononitrile to N-protected o-iminophenols; (4) Michael addition of nucleophiles to 2-iminochromene derivatives; and (5) organocatalyzed formal [4+2] cycloaddition reaction. In most cases, chiral thioureas have been found to be effective catalysts to promote the synthetic processes, and generally a bifunctional mode of action has been envisioned for them. In addition, squaramides and cinchona derivatives have been occasionally used as suitable catalysts for the substrates activation. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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