Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

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

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Publication Details

Journal
Organic Letters
Published
2024-12-26
DOI
https://doi.org/10.1021/acs.orglett.4c04224
Citations
12
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
3.00

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article

Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

Jun‐An Xiao, Wenjie Liang, Chenxiang Lin, Yumin Yang et al.
12 citations
Organic Letters
Oxidative Organic Chemistry Reactions
3.00
article

Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

Jun‐An Xiao, Wenjie Liang, Chenxiang Lin, Yumin Yang, Yang Liu, Wei‐Fang Su, Hongyan Jiang, Zhiping Liu, Lan Zheng, Wei Wang
article en
12 citations

Abstract

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

Organic LettersVol. 27(1)
Nanning Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 8%
Oxidative Organic Chemistry Reactions
3.00
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Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones — Jun‐An Xiao, Wenjie Liang, et al. · Organic Letters (2024) | TGRS Research Map | TGRS