CARMONA CARMONA, JOSÉ ALBERTO, Rodriguez-Salamanca, Patricia , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin
Si
Angew. Chem.-Int. Edit.
Article
Científica
16.1
5.3
28/08/2023
001029742700001
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.
Allylation; Asymmetric Catalysis; Axial Chirality; Iridium Catalysis; Quinolines