A formal (3 + 2) annulation–Cannizzaro cascade of bifunctional peroxides for the synthesis of dihydrofurans

Chen, Yiwei; Gao, Min; Xu, Qianlan; Zhang, Jiumeng; Hu, Lin

doi:10.1039/d4qo00215f

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00215f

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A formal (3 + 2) annulation–Cannizzaro cascade of bifunctional peroxides for the synthesis of dihydrofurans

Yiwei Chen,

Min Gao,

Qianlan Xu

et al.

Abstract: A complicated Michael addition-epoxidation-cyclization-Cannizzaro cascade of 2-fomylallyl peroxides and β-keto esters has been developed under mild KOH basic conditions, which produces a pair of 2,2-bis(hydroxymethyl) and 2-carboxyl-2-hydroxymethyl dihydrofurans in good...

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Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides

Feng,

Wang,

2024

Asian J Org Chem

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Isochroman is one of the powerful scaffolds which demonstrated various important biologically activities. Herein we represented the novel and versatile method for the synthesis of valuable isochroman spiropyrazolones of difunctional peroxides and pyrazolones via [1+5] annulation. This process represents a novel spiroisochroman synthesis protocol and is featured by good functional group compatibility, mild conditions and readily available substrates.

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Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides

Feng,

Wang,

2024

Asian J Org Chem

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A new tandem reaction of bifunctional peroxides enables the expedient synthesis of functionalized dihydrofurans

He,

Chen,

Zhao

et al. 2025

Org. Chem. Front.

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A formal (3 + 2) annulation–Cannizzaro cascade of bifunctional peroxides for the synthesis of dihydrofurans

Abstract: A complicated Michael addition-epoxidation-cyclization-Cannizzaro cascade of 2-fomylallyl peroxides and β-keto esters has been developed under mild KOH basic conditions, which produces a pair of 2,2-bis(hydroxymethyl) and 2-carboxyl-2-hydroxymethyl dihydrofurans in good...

Cited by 2 publications

References 39 publications

Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides

Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides

A new tandem reaction of bifunctional peroxides enables the expedient synthesis of functionalized dihydrofurans

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