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Dynamic Kinetic Resolution of Heterobiaryl Ketones by Zinc-Catalyzed Asymmetric Hydrosilylation

AuthorsCarmona, José A.; Hornillos, Valentín ; Ramírez-López, Pedro; Ros, Abel ; Iglesias-Sigüenza, Javier; Gómez-Bengoa, Enrique; Fernández, Rosario; Lassaletta, José M.
Issue Date2018
CitationAngewandte Chemie International Edition 57: 3777- 3781 (2018)
AbstractA 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.
Identifiersdoi: 10.1002/anie.201713200
issn: 1521-3773
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