Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

doi:10.1055/s-0036-1588987

Paper

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Published Mar 30, 2017 · Kensuke Kiyokawa, K. Takemoto, Shunsuke Yahata

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Abstract

Abstract The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Study Snapshot

This study presents an efficient method for synthesis of 4-substituted furan-2-ones using hypervalent iodine reagents, offering potential applications in organic chemistry and medicinal chemistry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

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References

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Acid activation in phenyliodine dicarboxylates enhances their reactivity in organic synthesis, with the PIDA-BF3 complex being the first to be isolated and its structure determined by X-ray diffraction.

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This new oxidative cyclization process can produce functionalized lactones and dihydrofuranaldehydes, with potential applications in organic synthesis and catalysis.

Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C–OH bond activation

Palladium-catalyzed C-OH bond activation efficiently produces 4-substituted-pyrones and 2(5H)-furanones in good yields under mild conditions.

Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

Bistributylstannyl-2(5H)-furanone 4a shows good selectivity in Stille reactions, leading to 4-substituted-3-stannyl-2(5H)-furanones in moderate yield.

A general method for alkylating 2(5H)-furanones; reduction of products to 3-, 2,3-, and 3,4-substituted furans

This study presents a general method for alkylating 2(5H)-furanones and reducing them to 3-, 2,3-, and 3,4-substituted furans in good yield.

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