Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/108062
Title: Expedient organocatalytic syntheses of 4-substituted pyrazolidines and isoxazolidines
Author: Yousfi, Tarek
Elliott, Alysha
Hanane, Messiad
Merdes, Rashid
Moyano i Baldoire, Albert
Keywords: Catàlisi asimètrica
Enantioselective catalysis
Issue Date: 1-Dec-2016
Publisher: MDPI
Abstract: 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.
Note: Reproducció del document publicat a: https://doi.org/10.3390/molecules21121655
It is part of: Molecules, 2016, vol. 21, p. 1655
Related resource: https://doi.org/10.3390/molecules21121655
URI: http://hdl.handle.net/2445/108062
ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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