Dynamic kinetic resolution of indole-based sulfenylated heterobiaryls by rhodium-catalyzed atroposelective reductive aldol reaction

Rodríguez-Franco, Carlos ; Ros, Abel ; Merino, Pedro (Universidad de Zaragoza) ; Fernández, Rosario ; Lassaletta, José M. ; Hornillos, Valentín

Resumen: A highly enantio- and diastereoselective dynamic kinetic resolution (DKR) of configurationally labile 3-aryl indole-2-carbaldehydes is described. The DKR proceeds via a Rh-catalyzed intermolecular asymmetric reductive aldol reaction with acrylate esters, with simultaneous generation of three stereogenic elements. The strategy relies on the labilization of the stereogenic axis that takes place thanks to a transient Lewis acid–base interaction (LABI) between the formyl group and a thioether moiety strategically located at the ortho′ position. The atropisomeric indole products present a high degree of functionalization and can be further converted to a series of axially chiral derivatives, thereby expanding their potential application in drug discovery and asymmetric catalysis.

Idioma: Inglés

DOI: 10.1021/acscatal.3c03422

Año: 2023

Publicado en: ACS CATALYSIS 13, 18 (2023), 12134-12141
ISSN: 2155-5435

Factor impacto JCR: 11.7 (2023)

Categ. JCR: CHEMISTRY, PHYSICAL rank: 21 / 178 = 0.118 (2023) - Q1 - T1

Factor impacto CITESCORE: 20.8 - Chemistry (all) (Q1) - Catalysis (Q1)

Factor impacto SCIMAGO: 3.847 - Chemistry (miscellaneous) (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/17R-34
Financiación: info:eu-repo/grantAgreement/ES/MCIU/FPU18-02677
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-106358GB-C21
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-106358GB-C22
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RYC-2017-22294

Tipo y forma: (Versión definitiva)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)