Simmons-Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates): Stereoselective Access to Functionalized Cyclopropyl Derivatives

Maruti Mali, Gangavaram V. M. Sharma, Subhash Ghosh*, Thierry Roisnel, Bertrand Carboni and Fabienne Berrée*

*Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India; Institut des Sciences Chimiques de Rennes, F-35000 Rennes, France, Email: subhashiict.res.in, fabienne.berreeuniv-rennes1.fr

M. Mali, G. V. M. Sharma, S. Ghosh, T. Roisnel, B. Carboni, F. Berrée, J. Org. Chem., 2022, 87, 7649-7657.

DOI: 10.1021/acs.joc.2c00152

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Abstract

A Simmon-Smith reaction of alkenyl 1,2-bis(boronates) enables the stereodefined synthesis of cyclopropyl-1,2-bis(boronates). Subsequent regioselective Suzuki-Miyaura couplings provide diversely tri- or tetra-substituted arylcyclopropanes in good yields.

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Key Words

Simmon-Smith reaction, cyclopropanes, arylation

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ID: J42-Y2022