Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes

Heng-Xian He, Feng Wu, Kun-Ju Wang, Lei Wang and Jian-Jun Feng ()
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Heng-Xian He: Hunan University
Feng Wu: Hunan University
Kun-Ju Wang: Hunan University
Lei Wang: Yangzhou University
Jian-Jun Feng: Hunan University

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract Although ring-opening reactions of bicyclo[1.1.0]butanes (BCBs) provide a reliable platform for synthesizing functionalized cyclobutanes, current methods frequently encounter challenges such as poor diastereoselectivity, regioselectivity issues, and a lack of α- and β‘-selective transformations. Herein, we report a catalyst-controlled, regiodivergent α- and β‘-selective hydrophosphination of acyl BCBs, which expands the chemical space of tertiary phosphines with multi-substituted cyclobutane backbones derived from identical starting materials. Utilizing a Cu(I) catalytic system, we achieve an α-selective nucleophilic addition to 1,3-disubstituted BCBs. This reaction exhibits a broad substrate scope under mild conditions, yielding valuable 1,1,3-functionalized cyclobutanes predominantly as single diastereoisomers. In contrast, the unusual β‘-selective pathway facilitated by a Cu(II) catalytic system produces 1,2,3-trisubstituted variants with up to >20:1 d.r. The developed method holds promise for accessing structurally diverse cyclobutanes with potential applications in medicinal chemistry and the design of organophosphorus catalysts.

Date: 2025
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DOI: 10.1038/s41467-025-61726-w

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