Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

Here, we develop a mild and scalable approach for the synthesis of 2-amino-bicyclo[2.1.1]hexanes <i>via</i> Lewis acid-catalyzed (3+2) cycloaddition of bicyclo[1.1.0]butanes (BCBs) with enamides. The practicality of this methodology has been demonstrated by scale-up reactions and product modifications, providing highly valuable aniline bioisosteres and structurally complex three-dimensional cyclic amines.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc02908b
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00

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article

Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

Huiyu Chen, Shaoxiong Yang, Yanren Zhu, Enfan Pu et al.
Chemical Communications
Cyclopropane Reaction Mechanisms
article

Cycloaddition of bicyclo[1.1.0]butanes with enamides for the efficient synthesis of 2-amino-bicyclo[2.1.1]hexanes

Huiyu Chen, Shaoxiong Yang, Yanren Zhu, Enfan Pu, Hongbin Zhang, Jingbo Chen, Yi Jin, Fang Zhang, P. Jiang
article en

Abstract

Here, we develop a mild and scalable approach for the synthesis of 2-amino-bicyclo[2.1.1]hexanes <i>via</i> Lewis acid-catalyzed (3+2) cycloaddition of bicyclo[1.1.0]butanes (BCBs) with enamides. The practicality of this methodology has been demonstrated by scale-up reactions and product modifications, providing highly valuable aniline bioisosteres and structurally complex three-dimensional cyclic amines.

Chemical CommunicationsVol. 61(61)
Yunnan University (CN), KU Leuven (BE)
National Natural Science Foundation of China
Openalex Percentile: Top 89%
Cyclopropane Reaction Mechanisms
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