Artículo
Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction
Autor/es | Rodríguez Franco, Carlos
Ros, Abel Merino, Pedro Fernández Fernández, Rosario Fátima Lassaletta, José M. Hornillos, Valentín |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2023-08-30 |
Fecha de depósito | 2024-05-22 |
Publicado en |
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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 ... 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. |
Agencias financiadoras | European funding (ERDF) Ministerio de Ciencia e Innovación (MICIN). España Gobierno regional de Aragón Junta de Andalucía |
Identificador del proyecto | P18-FR-3531
P18-FR-644 US-1262867 US-126090 17R-34 PID2019-106358GB-C21 PID2019-106358GB-C22 PID2019-104090RB-100 RYC-2017-22294 FPU18/02677 |
Cita | Rodríguez Franco, C., Ros, A., Merino, P., Fernández Fernández, R.F., Lassaletta, J.M. y Hornillos, V. (2023). Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction. ACS catalysis, 13 (18), 12134-12141. https://doi.org/10.1021/acscatal.3c03422. |
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