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Molecules 2016, 21(12), 1655;

Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines

Division de Biotechnologie Industrielle, Centre National de Recherche en Biotechnologie, Ali Mendjli Nouvelle Ville, UV 03 BP E73, Constantine 25000, Algeria
Laboratoire de Chimie Appliquée, Département de Chimie, Université 8 Mai 1945—Guelma, BP 401, Guelma 24000, Algeria
Institute for Molecular Biosciences, The University of Queensland, St. Lucia QLD 4072, Australia
Département de Génie de l’Environnement, Faculté de Génie des Procédés, Université de Constantine 3, Ali Mendjli Nouvelle Ville, BP72, Constantine 25000, Algeria
Departament de Química Inorgànica i Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, Barcelona 08028, Catalonia, Spain
Author to whom correspondence should be addressed.
Academic Editor: Raquel Herrera
Received: 9 November 2016 / Revised: 24 November 2016 / Accepted: 28 November 2016 / Published: 1 December 2016
(This article belongs to the Collection Recent Advances in Organocatalysis)
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The efficient organocatalytic synthesis of heterocyclic systems of biological relevance is a subject of growing interest. We have found that the pyrrolidine/benzoic acid-catalyzed reaction of α-substituted propenals such as methacrolein, 2-benzylpropenal and 2-(n-hexyl)propenal with activated hydrazines takes place in very good yields (83%–99.6%) under very mild conditions to afford 4-substituted pyrazolidin-3-ols (as diastereomer mixtures); subsequent oxidation with PCC affords the corresponding-4-substituted-3-pyrazolidinones in essentially quantitative yields. In a similar way, 4-substituted isoxazolidinones are obtained with N-Cbz-hydroxylamine as a reagent. The use of chiral diarylprolinol trimethylsilyl ethers as catalysts allows the synthesis of several of these compounds in optically active form, in some cases with excellent enantioselectivity (up to 96:4 er). A preliminary evaluation of the biological activity shows that some of these compounds exhibit interesting antibacterial and antifungal activities. View Full-Text
Keywords: asymmetric catalysis; isoxazolidinones; pyrazolidinones; organocatalysis; hydrazines; hydroxylamines; enals asymmetric catalysis; isoxazolidinones; pyrazolidinones; organocatalysis; hydrazines; hydroxylamines; enals

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Yousfi, T.; Elliott, A.; Hanane, M.; Merdes, R.; Moyano, A. Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines. Molecules 2016, 21, 1655.

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