Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl)Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation
José A. Carmona, Patricia Rodríguez‐Salamanca, Rosario Fernández, José M. Lassaletta, Valentı́n Hornillos
Abstract
An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes by transfer hydrogenative coupling of allyl acetate is disclosed. The allylation reaction takes place with simultaneous installation of central and axial chirality, reaching high diastereoselectivities and excellent enantiomeric excesses when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates occurs through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.
Topics & Concepts
RacemizationIridiumKinetic resolutionChemistryAldehydeCatalysisEnantiomerLewis acids and basesQuinolineTransfer hydrogenationEnantioselective synthesisCombinatorial chemistryOrganic chemistryRutheniumAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityChemical synthesis and alkaloids