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

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

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 arylcycloprop...

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Veröffentlicht in:Journal of organic chemistry 2022-06, Vol.87 (12), p.7649-7657
Hauptverfasser: Mali, Maruti, Sharma, Gangavaram V. M., Ghosh, Subhash, Roisnel, Thierry, Carboni, Bertrand, Berrée, Fabienne
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container_end_page 7657
container_issue 12
container_start_page 7649
container_title Journal of organic chemistry
container_volume 87
creator Mali, Maruti
Sharma, Gangavaram V. M.
Ghosh, Subhash
Roisnel, Thierry
Carboni, Bertrand
Berrée, Fabienne
description 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.
doi_str_mv 10.1021/acs.joc.2c00152
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title Simmons–Smith Cyclopropanation of Alkenyl 1,2-Bis(boronates): Stereoselective Access to Functionalized Cyclopropyl Derivatives
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