Heteropolyacid‐catalyzed Reaction of Epoxides with Ketones: Efficient Synthesis of 1,3‐Dioxolane Derivatives

He, Junyi; Gao, Feifei; Hua, Ruimao

doi:10.1002/cjoc.200591275

Cited by 9 publications

(6 citation statements)

References 20 publications

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“…Hydrolysis reactions proceeded with very good yields (>84 %) for acetonides 15 , 17 and 21 (entries 1, 2 and 5). Substrates 19 and 20 , however, were transformed into their corresponding diols in slightly lower yields (79 % for 12 and 81 % for 13 ), probably due to the high volatility of the starting acetonides [25,26] . It should be noted that neither of them required any further purification step by chromatography.…”

Section: Resultsmentioning

confidence: 97%

An Eco‐Friendly and Switchable Carbon‐Based Catalyst for Protection‐Deprotection of Vicinal Diols

et al. 2023

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Even though protection-free protocols represent a key principle of green chemistry, both protection and deprotection routes are indispensable strategies in synthetic pursuits, especially towards highly functionalized pharmaceuticals and agrochemicals, often decorated by promiscuous OH or NH groups, among others. Herein a sustainable carbon-based catalyst is reported that efficiently promotes the protection of 1,2-diols as isopropylidene ketals under heterogeneous conditions, affording products in high conversion and yields. Grafting of sulfonate groups onto the high-surface-area carbon creates a solid acid catalyst with high performance for acetalization under mild thermal conditions. Interestingly, the same catalyst can be employed for the inverse deprotection step leading to the parent diols with comparable efficiency. Along with a detailed catalyst's characterization, critical issues related to catalyst loading, reaction scope, and selectivity were thoroughly optimized. The catalyst can be recycled, and no impurities caused by leaching could be observed.

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Section: Resultsmentioning

confidence: 97%

An Eco‐Friendly and Switchable Carbon‐Based Catalyst for Protection‐Deprotection of Vicinal Diols

et al. 2023

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“…). The dioxolane can be formed from glycol or epoxide . The glycol is formed by hydroxylation of the epoxide in the presence of residual water .…”

Section: Resultsmentioning

confidence: 99%

“…heteropoly acids, HBF 4 and montmorillonites) and Lewis acids (e.g. SnCl 4 , TiCl 4 , CuSO 4 and BF 3 .O(C 2 H 5 ) 2 ) have been used as catalysts . Shan et al reported the ketalization and acetalization of carbonyl compounds with diols catalyzed by a carbon‐based solid acid, affording an average yield of 93% .…”

Section: Introductionmentioning

confidence: 99%

Ketalization of epoxidized methyl oleate using acidic resins

Pérez

Echeverri

Ríos

2016

J. Chem. Technol. Biotechnol

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BACKGROUND: Fatty acid dioxolanes can be used as bioplasticizers or biolubricants, replacing petroleum-derived products. Dioxolanes can be obtained by reaction of epoxides or glycols with ketones under acidic conditions. Brönsted and Lewis acids have been reported as catalysts of the reaction. However, acidic resins have not been used so far. These heterogeneous catalysts offer high activity, reusability as well as low price. In this work, ketalization of epoxidized methyl oleate with acetone was evaluated using acidic resins (Dowex-50WX2, Amberlyst-15 and Amberlite-IR120) at low temperature (35-55 ∘ C).

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“…The direct conversion of epoxides to the corresponding acetonides has been described with the use of different Lewis acid catalysts. Among the most recent catalysts, with various degrees of success in terms of yield and selectivity, are anhydrous SnCl 2 ,2 tin( IV ) tetraphenylporphyrin perchlorate,3 2,4,4,6‐tetrabromo‐2,5‐cyclohexadienone,4 bismuth( III ) salts,5 various titanium complexes,6 [(C 5 Me 5 )Ir(NaMe) 3 ],7 RuCl 3 ,8 CH 3 ReO 3 ,9 Cu(OTf) 2 ,10,11Er(OTf) 3 ,12 BF 3 · Et 2 O,13 LiBF 4 ,14 and heteropolyacids 15. Many of these catalysts are strong Lewis acids and are not suitable in the presence of other functional groups.…”

Section: Introductionmentioning

confidence: 99%

A Mild Stereo‐ and Enantiospecific Conversion of 2,3‐Diaryl‐Substituted Oxiranes into 2,2‐Dimethyl‐1,3‐Dioxolanes by an Acetone/Amberlyst 15 System

et al. 2006

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Amberlyst 15 is an efficient catalyst for the reaction of aryl‐substituted oxiranes with acetone to prepare 2,2‐dimethyl‐1,3‐dioxolanes in high yields. trans‐2,3‐Diaryloxiranes afford trans‐acetonides enantiospecifically at room temperature, and the use of enantiopure 2,3‐diaryloxiranes results in no loss of stereochemical integrity in the resulting trans‐acetonides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Heteropolyacid‐catalyzed Reaction of Epoxides with Ketones: Efficient Synthesis of 1,3‐Dioxolane Derivatives

Abstract: An efficient method for the preparation of 1,3-dioxolanes via the coupling of epoxides with ketones catalyzed by heteropolyacids at ambient temperature has been described.

Cited by 9 publications

References 20 publications

An Eco‐Friendly and Switchable Carbon‐Based Catalyst for Protection‐Deprotection of Vicinal Diols

An Eco‐Friendly and Switchable Carbon‐Based Catalyst for Protection‐Deprotection of Vicinal Diols

Ketalization of epoxidized methyl oleate using acidic resins

A Mild Stereo‐ and Enantiospecific Conversion of 2,3‐Diaryl‐Substituted Oxiranes into 2,2‐Dimethyl‐1,3‐Dioxolanes by an Acetone/Amberlyst 15 System

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