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Simmons-Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates): Stereoselective Access to Functionalized Cyclopropyl Derivatives. 2022
Maruti Mali, and
Gangavaram V M Sharma, and
Subhash Ghosh, and
Thierry Roisnel, and
Bertrand Carboni, and
Fabienne Berrée
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
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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