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A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

ABSTRACT: Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral (10)B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.

SUBMITTER: Sun C

PROVIDER: S-EPMC4021567 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

Sun Chunrui C Potter Bowman B Morken James P JP

Journal of the American Chemical Society 20140224 18

Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral (10)B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of ...[more]

PMID: 24564423

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