Diastereodivergent Synthesis of trans- and cis-Cyclobutane-Based γ-Aminobutyric Acid Derivatives via Cu(OTf)2-Catalyzed Strain-Release Reactions of Bicyclo[1.1.0]butanes

Ling Chen; Jun-Cheng Jin; Qi-Guo Zheng; Jian Zhang; Wei-Ping Deng

doi:10.1002/cjoc.70261

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) :3476 -3482. DOI: 10.1002/cjoc.70261

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Diastereodivergent Synthesis of trans- and cis-Cyclobutane-Based γ-Aminobutyric Acid Derivatives via Cu(OTf)₂-Catalyzed Strain-Release Reactions of Bicyclo[1.1.0]butanes

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Abstract

Herein, we report the synthesis of multifunctionalized trans- and cis-cyclobutane-based γ-aminobutyric acid derivatives via diastereodivergent Cu(OTf)₂-catalyzed strain-release reactions of bicyclo[1.1.0]butanes with amines. This protocol enables precise control of product configuration via ligand selection, providing a powerful tool for modulating the stereochemistry of the resulting compounds. In addition, the synthesized cyclobutane-based γ-aminobutyric acid derivatives significantly expand substituent diversity, thereby greatly enhancing molecular complexity. The method proceeds under mild conditions and exhibits excellent tolerance toward a broad range of functional groups, making it a versatile platform for the development of novel drug candidates.

Keywords

Diastereodivergent synthesis / γ-Aminobutyric acids / Bicyclo[1.1.0]butanes / Strain-release / Lewis acid catalysis

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Ling Chen, Jun-Cheng Jin, Qi-Guo Zheng, Jian Zhang, Wei-Ping Deng. Diastereodivergent Synthesis of trans- and cis-Cyclobutane-Based γ-Aminobutyric Acid Derivatives via Cu(OTf)₂-Catalyzed Strain-Release Reactions of Bicyclo[1.1.0]butanes. Chinese Journal of Chemistry, 2025, 43(24): 3476-3482 DOI:10.1002/cjoc.70261