Ligand-controlled regiodivergent aminocarbonylation of cyclobutanols toward 1,1- and 1,2-substituted cyclobutanecarboxamides

Four-membered carbocycles are among the most sought-after backbones which are commonly found in biologically active molecules. However, difficulties on their producing are existing due to its highly strained ring system. On the other hand, cyclobutanols can be straightforwardly prepared and can serves as precursors for synthesizing cyclobutane derivatives. Here we report an example of regioselective aminocarbonylation of cyclobutanols in which the cyclobutane core remained intact. The method exhibits good functional group compatibility, as well as high regio- and stereoselectivity, offering new pathways for synthesizing several pharmaceuticals. Furthermore, this strategy enables the rapid installation of cyclobutane as a conformational restricted skeleton, greatly facilitating direct access to valuable drug molecules that require conformational restriction.

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Publication Details

Journal
Nature Communications
Published
2024-10-31
DOI
https://doi.org/10.1038/s41467-024-53571-0
Citations
9
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.87

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article

Ligand-controlled regiodivergent aminocarbonylation of cyclobutanols toward 1,1- and 1,2-substituted cyclobutanecarboxamides

Xiao‐Feng Wu, Yanhua Zhao, Xing-Wei Gu
9 citations
Nature Communications
Fluorine in Organic Chemistry
1.87
article

Ligand-controlled regiodivergent aminocarbonylation of cyclobutanols toward 1,1- and 1,2-substituted cyclobutanecarboxamides

Xiao‐Feng Wu, Yanhua Zhao, Xing-Wei Gu
article en
9 citations

Abstract

Four-membered carbocycles are among the most sought-after backbones which are commonly found in biologically active molecules. However, difficulties on their producing are existing due to its highly strained ring system. On the other hand, cyclobutanols can be straightforwardly prepared and can serves as precursors for synthesizing cyclobutane derivatives. Here we report an example of regioselective aminocarbonylation of cyclobutanols in which the cyclobutane core remained intact. The method exhibits good functional group compatibility, as well as high regio- and stereoselectivity, offering new pathways for synthesizing several pharmaceuticals. Furthermore, this strategy enables the rapid installation of cyclobutane as a conformational restricted skeleton, greatly facilitating direct access to valuable drug molecules that require conformational restriction.

Nature CommunicationsVol. 15(1)
Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Leibniz Institute for Catalysis (DE), Dalian National Laboratory for Clean Energy (CN)
Chinese Academy of Sciences
Openalex Percentile: Top 16%
Fluorine in Organic Chemistry
1.87
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