Palladium-Catalyzed\nStrain-Enabled [2π + 2σ]\nCycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

A palladium-catalyzed\n[2π + 2σ] cycloaddition\nof vinyl\nbicyclo[1.1.0]butanes with methyleneindolinones has been developed.\nThe reaction enables the construction of spirobicyclo[2.1.1]hexanes\nbearing an all-carbon quaternary center in moderate to good yields\nwith excellent diastereoselectivities. This method features a broad\nsubstrate scope with good functional group compatibility. The practical\nutility of this protocol was further demonstrated by gram-scale synthesis\nand postsynthetic transformations of desired product.

Publication Details

Journal
Figshare
Published
2024-12-26
DOI
https://doi.org/10.1021/acs.orglett.4c04224.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

Palladium-Catalyzed\nStrain-Enabled [2π + 2σ]\nCycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

Figshare
Cyclopropane Reaction Mechanisms
article

Palladium-Catalyzed\nStrain-Enabled [2π + 2σ]\nCycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

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Abstract

A palladium-catalyzed\n[2π + 2σ] cycloaddition\nof vinyl\nbicyclo[1.1.0]butanes with methyleneindolinones has been developed.\nThe reaction enables the construction of spirobicyclo[2.1.1]hexanes\nbearing an all-carbon quaternary center in moderate to good yields\nwith excellent diastereoselectivities. This method features a broad\nsubstrate scope with good functional group compatibility. The practical\nutility of this protocol was further demonstrated by gram-scale synthesis\nand postsynthetic transformations of desired product.

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Cyclopropane Reaction Mechanisms
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Palladium-Catalyzed\nStrain-Enabled [2π + 2σ]\nCycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones · Figshare (2024) | TGRS Research Map | TGRS