Título Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
Autores CARMONA CARMONA, JOSÉ ALBERTO, Rodriguez-Salamanca, Patricia , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin
Publicación externa Si
Medio Angew. Chem.-Int. Edit.
Alcance Article
Naturaleza Científica
Cuartil JCR 1
Cuartil SJR 1
Impacto JCR 16.1
Impacto SJR 5.3
Fecha de publicacion 28/08/2023
ISI 001029742700001
DOI 10.1002/anie.202306981
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.
Palabras clave Allylation; Asymmetric Catalysis; Axial Chirality; Iridium Catalysis; Quinolines
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