Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation ; day:17 ; month:07 ; year:2023 ; extent:7
Angewandte Chemie ; (17.07.2023) (gesamt 7)

Creator: Carmona, José A.
Rodríguez‐Salamanca, Patricia
Fernández, Rosario
Lassaletta, José M.
Hornillos, Valentín

DOI: 10.1002/ange.202306981

URN: urn:nbn:de:101:1-2023071815074513742188

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:51 AM CEST

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Associated

Carmona, José A.
Rodríguez‐Salamanca, Patricia
Fernández, Rosario
Lassaletta, José M.
Hornillos, Valentín

Other Objects (12)

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Iridium-Catalyzed Asymmetric Hydroxymethylation

Iridium-Catalyzed Asymmetric Hydroxymethylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Iridium-Catalyzed Asymmetric Hydroxymethylation

Iridium-Catalyzed Asymmetric Hydroxymethylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl) Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Iridium‐Catalyzed Enantioselective Intermolecular Indole C2‐Allylation

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Ketone Enolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Iridium(I)-Catalyzed Allylation of Sodium 2-Aminobenzenethiolates

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Enantioselective Rhodium-Catalyzed α-Allylation of Aldehydes

Iridium-Catalyzed Asymmetric Hydroxymethylation

Iridium-Catalyzed Asymmetric Hydroxymethylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Azides and Nitriles in Palladium-Catalyzed Decarboxylative Allylation

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions

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