Dynamic Kinetic Resolution of 2‐(Quinolin‐8‐yl)Benzaldehydes: Atroposelective Iridium‐Catalyzed Transfer Hydrogenative Allylation-Reference-Cited by-同舟云学术

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

Published:2023-07-17 Issue:35 Volume:135 Page:
ISSN:0044-8249
Container-title:Angewandte Chemie
language:en
Short-container-title:Angewandte Chemie

Author:

Carmona José A.¹^ORCID,Rodríguez‐Salamanca Patricia¹^ORCID,Fernández Rosario²^ORCID,Lassaletta José M.¹^ORCID,Hornillos Valentín¹²^ORCID

Affiliation:

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

AbstractAn 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.

Funder

Ministerio de Ciencia e Innovación

Junta de Andalucía

Universidad de Sevilla

Publisher

Wiley

Subject

General Medicine

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.202306981

Reference90 articles.

2. Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products