Synthesis and Nucleophilic Ring-Opening of 1,1-Dicyanocyclopropanes: Accessing β-Aminocarbonyl Derivatives from Olefins

We report an atom-transfer radical addition-ring closure sequence for the preparation of 1,1-dicyanocyclopropane electrophiles and demonstrate their nucleophilic ring-opening with alkyl amines under mild conditions. The resulting aminomalononitrile products were converted to complex β-aminocarbonyl derivatives in one pot under aerobic conditions.

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Publication Details

Journal
Organic Letters
Published
2025-05-27
DOI
https://doi.org/10.1021/acs.orglett.5c00395
Citations
2
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
1.87

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article

Synthesis and Nucleophilic Ring-Opening of 1,1-Dicyanocyclopropanes: Accessing β-Aminocarbonyl Derivatives from Olefins

Adrián Gómez‐Suárez, Stefan F. Kirsch, Sebastian Govaerts, Jan Lukas Mayer-Figge et al.
2 citations
Organic Letters
Cyclopropane Reaction Mechanisms
1.87
article

Synthesis and Nucleophilic Ring-Opening of 1,1-Dicyanocyclopropanes: Accessing β-Aminocarbonyl Derivatives from Olefins

Adrián Gómez‐Suárez, Stefan F. Kirsch, Sebastian Govaerts, Jan Lukas Mayer-Figge, Mohit Chotia
article en
2 citations

Abstract

We report an atom-transfer radical addition-ring closure sequence for the preparation of 1,1-dicyanocyclopropane electrophiles and demonstrate their nucleophilic ring-opening with alkyl amines under mild conditions. The resulting aminomalononitrile products were converted to complex β-aminocarbonyl derivatives in one pot under aerobic conditions.

Organic LettersVol. 27(22)
University of Wuppertal (DE)
Deutsche Forschungsgemeinschaft
Openalex Percentile: Top 15%
Cyclopropane Reaction Mechanisms
1.87
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