Dynamic kinetic resolution of 2-(Quinolin-8-yl)benzaldehydes: atroposelective iridium-catalyzed transfer hydrogenative allylation

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 dia...

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Bibliographic Details
Authors: Carmona, José A., Rodríguez Salamanca, Patricia, Fernández Fernández, Rosario Fátima, Lassaletta, José M., Hornillos, Valentín
Format: article
Status:Published version
Publication Date:2023
Country:España
Institution:Universidad de Sevilla (US)
Repository:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/158792
Online Access:https://hdl.handle.net/11441/158792
https://doi.org/10.1002/anie.202306981
Access Level:Open access
Keyword:Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
Description
Summary: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.

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