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. 2022 Jun 17;87(12):7649-7657.
doi: 10.1021/acs.joc.2c00152. Epub 2022 May 31.

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

Maruti Mali  1   2 , Gangavaram V M Sharma  1 , Subhash Ghosh  1   2 , Thierry Roisnel  3 , Bertrand Carboni  3 , Fabienne Berrée  3
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Free article

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

Maruti Mali et al. J Org Chem. .
Free article

Abstract

A Simmons-Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis(boronates) has been developed starting from the corresponding alkenes. The resulting compounds were then subjected to regioselective Suzuki-Miyaura couplings to produce diversely tri- or tetra-substituted arylcyclopropanes in good yields. Further functionalization with 2-lithiothiophene provided 1,2-bis(aryl)cyclopropanes.

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