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Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.

ABSTRACT: Herein, we describe the catalytic enantioselective cross-coupling of 1,2-bisboronic esters. Prior work on group specific cross coupling is limited to the use of geminal bis-boronates. This desymmetrization provides a novel approach to prepare enantioenriched cyclopropyl boronates with three contiguous stereocenters, that could be further derivatized through selective functionalization of the carbon-boron bond. Our results suggest that transmetallation, which is the enantiodetermining step, takes place with retention of stereochemistry at carbon.

SUBMITTER: Teresa J

PROVIDER: S-EPMC9906671 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.

Teresa Javier J Velado Marina M Fernández de la Pradilla Roberto R Viso Alma A Lozano Blanca B Tortosa Mariola M

Chemical science 20230113 6

Herein, we describe the catalytic enantioselective cross-coupling of 1,2-bisboronic esters. Prior work on group specific cross coupling is limited to the use of geminal bis-boronates. This desymmetrization provides a novel approach to prepare enantioenriched cyclopropyl boronates with three contiguous stereocenters, that could be further derivatized through selective functionalization of the carbon-boron bond. Our results suggest that transmetallation, which is the enantiodetermining step, takes ...[more]

PMID: 36794195

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