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Symmetry
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Asymmetric Organocatalysis
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Asymmetric Organocatalysis

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

Deadline for manuscript submissions: closed (31 March 2011) | Viewed by 41668

Special Issue Editor

Prof. Dr. Svetlana Tsogoeva

E-Mail Website
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,

Evidently, enantiomers of bioactive compounds often have very different and, even opposite pharmacologic effects. Hitherto, many successful strategies were invented by chemists in order to obtain enantiomerically pure drugs and/or their intermediates.

Asymmetric organocatalysis, which is a powerful and environmentally friendly new methodology, facilitates strategies that provide an alternative to the conventional processes, which use transition-metal-complexes.

In many cases, the effectiveness of organocatalysts relies on covalent bonding: e.g. enamine/iminium ion activation by Lewis basic secondary or primary amines, or on the hydrogen bonding interactions: e.g. non-covalent catalysis with ureas and thioureas, diols, etc. Over the past years, a remarkable number of new enantioselective reactions subject to Brønsted- or Lewis-acid catalysis have been identified. Specifically, research has been focused on bi- and multi-functional catalysts containing Lewis or Brønsted basic moieties in combination with additional Lewis/Brønsted acidic functionality or hydrogen bond donors.Another fascinating organocatalytic system uses chiral phase-transfer catalysts (PTC).

Contributions are invited on all types of asymmetric organocatalysis and include:

  • covalent and non-covalent organocatalysis,
  • Lewis- or Brønsted-base organocatalysis,
  • Brønsted- or Lewis-acid organocatalysis,
  • asymmetric PTC,
  • bi- and multi-functional organocatalysis.

Prof. Dr. Svetlana Tsogoeva
Guest Editor

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Published Papers (5 papers)

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Research

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179 KiB  
Article
Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (−)-(S)-Brevicolline as an Organocatalyst
by Fliur Macaev, Natalia Sucman, Felix Shepeli, Marina Zveaghintseva and Vsevolod Pogrebnoi
Symmetry 2011, 3(2), 165-170; https://doi.org/10.3390/sym3020165 - 20 Apr 2011
Cited by 25 | Viewed by 6262
Abstract
The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro[oxindole-3,4'-4'H-pirane] [...] Read more.
The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro[oxindole-3,4'-4'H-pirane] derivatives in an optically active form in very good to excellent yields. Full article
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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134 KiB  
Article
Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones
by Masanori Yoshida, Keisuke Hirama, Mao Narita and Shoji Hara
Symmetry 2011, 3(2), 155-164; https://doi.org/10.3390/sym3020155 - 8 Apr 2011
Cited by 17 | Viewed by 6211
Abstract
Asymmetric Michael addition of carbon nucleophiles, nitroalkanes and a β-ketoester, to enones was investigated by using a primary amino acid lithium salt as a catalyst. Full article
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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Review

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330 KiB  
Review
Prolinethioamides versus Prolinamides in Organocatalyzed Aldol Reactions—A Comparative Study
by Dorota Gryko, Mikołaj Chromiński and Dominika J. Pielacińska
Symmetry 2011, 3(2), 265-282; https://doi.org/10.3390/sym3020265 - 1 Jun 2011
Cited by 18 | Viewed by 6578
Abstract
Various organocatalysts have been developed for the aldol reaction but particular attention has been paid to prolinamide derivatives. They are easy to prepare and their catalytic activity can be readily tuned through structural modification. In this review, the comparison of catalytic activities between [...] Read more.
Various organocatalysts have been developed for the aldol reaction but particular attention has been paid to prolinamide derivatives. They are easy to prepare and their catalytic activity can be readily tuned through structural modification. In this review, the comparison of catalytic activities between prolinethioamides and their respective amides in direct asymmetric aldol reactions is presented. Full article
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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1519 KiB  
Review
Organocatalytic Enantioselective Henry Reactions
by Yolanda Alvarez-Casao, Eugenia Marques-Lopez and Raquel P. Herrera
Symmetry 2011, 3(2), 220-245; https://doi.org/10.3390/sym3020220 - 23 May 2011
Cited by 116 | Viewed by 10985
Abstract
A large number of interesting organocatalytic enantioselective protocols have been explored and successfully applied in the last decade. Among them, the Henry (nitroaldol) reaction represents a powerful carbon-carbon bond-forming procedure for the preparation of valuable synthetic intermediates, such as enantioenriched nitro alcohols, which [...] Read more.
A large number of interesting organocatalytic enantioselective protocols have been explored and successfully applied in the last decade. Among them, the Henry (nitroaldol) reaction represents a powerful carbon-carbon bond-forming procedure for the preparation of valuable synthetic intermediates, such as enantioenriched nitro alcohols, which can be further transformed in a number of important nitrogen and oxygen-containing compounds. This area of research is still in expansion and a more complex version of this useful process has recently emerged, the domino Michael/Henry protocol, affording highly functionalized cycles with multiple stereogenic centers. Full article
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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457 KiB  
Review
Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones
by Renato Dalpozzo, Giuseppe Bartoli and Giorgio Bencivenni
Symmetry 2011, 3(1), 84-125; https://doi.org/10.3390/sym3010084 - 22 Mar 2011
Cited by 32 | Viewed by 10360
Abstract
The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field [...] Read more.
The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field and has been explored in recent years. At the same time, asymmetric Diels-Alder reactions have been developed and often a mechanism has been demonstrated to be a double addition rather than synchronous. This review aims to cover literature up to the end of 2010, describing all the different organocatalytic asymmetric 1,4-conjugate additions even if they are listed as transfer hydrogenation, cycloadditions or desymmetrization of aromatic compounds. Full article
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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