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Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation |
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| Authors: | Dr José A Carmona Dr Patricia Rodríguez-Salamanca Prof Rosario Fernández Prof José M Lassaletta Dr Valentín Hornillos |
| Institution: | 1. Instituto Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/Américo Vespucio 49, 41092 Sevilla, Spain;2. Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/Prof. García González 1, 41012 Sevilla, Spain |
| 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. |
| Keywords: | Allylation Asymmetric Catalysis Axial Chirality Iridium Catalysis Quinolines |