γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water

Floresta, Giuseppe; Talotta, Carmen; Gaeta, Carmine; Rosa, Margherita De; Chiacchio, Ugo; Neri, Placido; Rescifina, Antonio

doi:10.1021/acs.joc.7b00227

Cited by 35 publications

(10 citation statements)

References 51 publications

(61 reference statements)

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“…Furthermore, in silico studies were used to rationalize the reaction stereoselectivity outcome and to improve it by the choice of proper substrates able to interact with the cyclodextrin through hydrogen bond interactions. In fact, the calculations supported an inclusion mode with the insertion of phenyl ring of styrene 32 within the cavity pointing to the down rim and with the phenyl of nitrone 31 protruding out the cavity at the height of secondary OH groups in the upper rim (Floresta et al, 2017 ).…”

Section: Reaction Organocatalyzed By Cavity-containing Macrocyclic Scmentioning

confidence: 95%

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

et al. 2018

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In the last decades many efforts have been devoted to design supramolecular organocatalysts able to work in water as the reaction medium. The use of water as solvent provides promising benefits with respect to environmental impact. In this context, macrocyclic compounds played a role of primary importance thanks to their ease of synthesis and their molecular recognition abilities toward the reactants. The aim of this review is to give an overview of the recent advances in the field of supramolecular organocatalysis in water, focusing the attention on calixarene and cyclodextrins derivatives. Calixarenes and cyclodextrins, thanks to their hydrophobic cavities, are able to host selectively the substrates isolating they from the reaction environment. In addition, the synthetic versatilities of these macrocycles permits to introduce useful functional groups in close proximity of the hydrophobic binding sites. Regarding the cyclodextrins (CDs), we have here reviewed the their most recent uses as organocatalysts for the synthesis of heterocyclic compounds, in multi-component reactions and in carbon-carbon bond forming reactions. Examples have been reported in which CD catalysts are able to drive the regiochemistry of common organic reactions. In addition, cyclodextrins bearing catalytically active chiral groups, have shown excellent enantioselectivity in the catalysis of organic reactions. Recently reported results have shown that calixarene derivatives are able to accelerate organic reaction under “on-water” conditions with a significant selectivity toward the reactants. Under “on-water conditions” the hydrophobic effect, induced by insoluble calixarene derivatives, forces the reactants and the catalyst to aggregate and thus accelerating the reaction between them thanks to an amplification of weak secondary interactions. Regarding the use of water-soluble calixarene organocatalysts, we have here reviewed their role in the acceleration of common organic reactions.

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Section: Reaction Organocatalyzed By Cavity-containing Macrocyclic Scmentioning

confidence: 95%

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

et al. 2018

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“…A catalytic amount of γ-cyclodextrin (γ-CD) has been used by G. Floresta et al, to produce 3,5-diarylisoxazolidines via the 1,3-dipolar cycloaddition of several p -substituted nitrones, styrenes and cinnamate derivatives (Floresta et al, 2017). The cyclodextrin cavity acted as a reactor and heating at 100°C for 8–12 h gave a set of derivatives in good yields with moderate to excellent diastereoselectivity.…”

Section: 3-dipolar Cycloaddition In Watermentioning

confidence: 99%

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

et al. 2019

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The aim of this review is to provide an overview of green protocols for the organic synthesis of heterocycles via 1,3-dipolar cycloaddition. Particular attention has been devoted to the use of green solvents; reactions performed in ionic liquids, fluorinated solvents and water have been included. Also explored are several protocols that make use of catalyst-free reaction conditions, the use of microwave irradiation and activation by light exposure. Improvements over commonly used organic solvents will be underlined in order to highlight environmental protection aspects and enhancements in regio- and stereo-selectivity.

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“…γ‐Cyclodextrin (γ‐CD) was used as a catalyst for 1,3‐dipolar cycloaddition of nitrones with different styrenes and cinnamates on water . Different para ‐substituted nitrones as the dipole reacted effectively with different styrenes or cinnamates as the dipolarophile to afford 3,5‐diarylisoxazolidines in high yields with good‐to‐excellent diastereomeric excess (up to >95%) and catalyst reusability (Scheme ).…”

Section: Cycloaddition Reactions On Watermentioning

confidence: 99%

Recent Advances and Prospects of Organic Reactions “On Water”

et al. 2019

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Organic reactions “On water” is a rapidly developing area over the past few years. Many important classes of reactions like cross‐coupling reactions, pericyclic reactions, C−H activations etc. were performed on water and have shown tremendous increase in the reaction rates due to the potential hydrogen bonding capacity of water. This review focuses on the recent trends and developments in the field of on water reactions applied to organic synthesis and covers literature from 2016–2019.

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γ-Cyclodextrin as a Catalyst for the Synthesis of 2-Methyl-3,5-diarylisoxazolidines in Water

Cited by 35 publications

References 51 publications

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

Recent Advances and Prospects of Organic Reactions “On Water”

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