Regiodivergent formal [4+2] cycloaddition of nitrosoarenes with furanyl cyclopropane derivatives as 4π components

Cyclopropanes are commonly used as valuable 3-carbon building blocks. Herein, we disclose a different reactivity pattern of furanyl cyclopropanes, which serve as a 4-carbon component in Lewis acid-promoted [4+2] cycloadditions with nitrosoarenes to afford 1,2-oxazine derivatives. Importantly, the regioselectivity of the cycloaddition reaction can be controlled by the appropriate choice of the Lewis acid.

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Publication Details

Journal
Chemical Communications
Published
2024-12-16
DOI
https://doi.org/10.1039/d4cc05662k
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

Regiodivergent formal [4+2] cycloaddition of nitrosoarenes with furanyl cyclopropane derivatives as 4π components

R. Vicente, Sergio Mata, Luís A. López, Darío Coto
Chemical Communications
Cyclopropane Reaction Mechanisms
article

Regiodivergent formal [4+2] cycloaddition of nitrosoarenes with furanyl cyclopropane derivatives as 4π components

R. Vicente, Sergio Mata, Luís A. López, Darío Coto
article en

Abstract

Cyclopropanes are commonly used as valuable 3-carbon building blocks. Herein, we disclose a different reactivity pattern of furanyl cyclopropanes, which serve as a 4-carbon component in Lewis acid-promoted [4+2] cycloadditions with nitrosoarenes to afford 1,2-oxazine derivatives. Importantly, the regioselectivity of the cycloaddition reaction can be controlled by the appropriate choice of the Lewis acid.

Chemical CommunicationsVol. 61(7)
Universidad de Oviedo (ES)
Openalex Percentile: Top 83%
Cyclopropane Reaction Mechanisms
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