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Difunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins

Steven H. Bennett, Alexander Fawcett, Elliott H. Denton, Tobias Biberger, Valerio Fasano, Nils Winter and Varinder K. Aggarwal*

*School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom, Email:

S. H. Bennett, A. Fawcett, E. H. Denton, T. Biberger, V. Fasano, N. Winter, V. K. Aggarwal, J. Am. Chem. Soc., 2020, 142, 16766-16775.

DOI: 10.1021/jacs.0c07357

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Highly strained bicyclo[1.1.0]butyl boronate complexes, which were prepared by reacting boronic esters with bicyclo[1.1.0]butyl lithium, react with a wide range of electrophiles to form a diverse set of 1,1,3-trisubstituted cyclobutanes with high diastereoselectivity via difunctionalization of the strained central C-C σ-bond of the bicyclo[1.1.0]butyl unit.

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proposed reaction pathway

Key Words

alkylboronates, cyclobutanes

ID: J48-Y2020