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

Maruti Mali (1, 2, 3) , Gangavaram V. M. Sharma (1, 3) , Subhash Ghosh (1, 2, 3) , Thierry Roisnel (4) , Bertrand Carboni (4) , Fabienne Berrée (4)

1 CSIR - Council of Scientific and Industrial Research [India]
2 AcSIR - Academy of Scientific and Innovative Research [Ghaziabad, India]
3 IICT - CSIR Indian Institute of Chemical Technology [Hyderabad]
4 ISCR - Institut des Sciences Chimiques de Rennes

A Simmons-Smith stereodefined procedure for thesynthesis of cyclopropyl-1,2-bis(boronates) has been developedstarting from the corresponding alkenes. The resulting compoundswere then subjected to regioselective Suzuki-Miyaura couplings toproduce diversely tri- or tetra-substituted arylcyclopropanes in goodyields. Further functionalization with 2-lithiothiophene provided 1,2-bis(aryl)cyclopropanes.

Domaines: Chimie organique

Maruti Mali, Gangavaram V. M. Sharma, Subhash Ghosh, Thierry Roisnel, Bertrand Carboni, et al.. Simmons-Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates):Stereoselective Access to Functionalized Cyclopropyl Derivatives br. Journal of Organic Chemistry, 2022, 87 (12), pp.7649-7657. ⟨10.1021/acs.joc.2c00152⟩. ⟨hal-03715394⟩