Dynamic Kinetic Resolution of Heterobiaryl Ketones by Zinc‐Catalyzed Asymmetric Hydrosilylation |
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| Authors: | Dr Valentín Hornillos José A Carmona Dr Abel Ros Dr Javier Iglesias‐Sigüenza Dr Joaquín López‐Serrano Prof Rosario Fernández Prof José M Lassaletta |
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| Institution: | 1. Instituto Investigaciones Químicas (CSIC-US), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Sevilla, Spain;2. Departamento de Química Orgánica (Universidad de Sevilla), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Sevilla, Spain;3. Departamento de Química Inorgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA)., Universidad de Sevilla and Instituto de Investigaciones Científicas (CSIC-US), Sevilla, Spain |
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| Abstract: | A diastereo‐ and highly enantioselective dynamic kinetic resolution (DKR) of configurationally labile heterobiaryl ketones is described. The DKR proceeds by zinc‐catalyzed hydrosilylation of the carbonyl group, thus leading to secondary alcohols bearing axial and central chirality. The strategy relies on the labilization of the stereogenic axis that takes place thanks to a Lewis acid–base interaction between a nitrogen atom in the heterocycle and the ketone carbonyl group. The synthetic utility of the methodology is demonstrated through stereospecific transformations into either N,N‐ligands or appealing axially chiral, bifunctional thiourea organocatalysts. |
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| Keywords: | asymmetric catalysis axial chirality dynamic kinetic resolution hydrosilylation ligand design |
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