Synthesis of Borylated Carbocycles by [2 + 2]-Cycloadditions and Photo-Ene Reactions

Synthesis of Borylated Carbocycles by [2 + 2]-Cycloadditions and Photo-Ene Reactions

Saturated bicyclic compounds make up a valuable class of building blocks in the development of agrochemicals and pharmaceuticals. Here, we present the synthesis of borylated bicyclo[2.1.1]­hexanes via crossed [2 + 2]-cycloaddition. Due to the presence of the C–B bond, a variety of structures can be...

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Veröffentlicht in:Journal of the American Chemical Society 2024-04, Vol.146 (14), p.10142-10149
Hauptverfasser: Posz, Jarett M., Sharma, Neetu, Royalty, Paige A., Liu, Yanyao, Salome, Christophe, Fessard, Thomas C., Brown, M. Kevin
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agrochemicals
diastereoselective synthesis
drugs
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container_end_page 10149
container_issue 14
container_start_page 10142
container_title Journal of the American Chemical Society
container_volume 146
creator Posz, Jarett M.
Sharma, Neetu
Royalty, Paige A.
Liu, Yanyao
Salome, Christophe
Fessard, Thomas C.
Brown, M. Kevin
description Saturated bicyclic compounds make up a valuable class of building blocks in the development of agrochemicals and pharmaceuticals. Here, we present the synthesis of borylated bicyclo[2.1.1]­hexanes via crossed [2 + 2]-cycloaddition. Due to the presence of the C–B bond, a variety of structures can be easily prepared that are not accessible by other methods. Moreover, a rare photo-ene reaction is also disclosed, allowing for the diastereoselective synthesis of trisubstituted borylated cyclopentanes.
doi_str_mv 10.1021/jacs.4c01557
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subjects agrochemicals
diastereoselective synthesis
drugs
title Synthesis of Borylated Carbocycles by [2 + 2]-Cycloadditions and Photo-Ene Reactions
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