Article
Dynamic kinetic resolution of 2-(Quinolin-8-yl)benzaldehydes: atroposelective iridium-catalyzed transfer hydrogenative allylation
Author/s | Carmona, José A.
Rodríguez Salamanca, Patricia Fernández Fernández, Rosario Fátima Lassaletta, José M. Hornillos, Valentín |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2023-06-30 |
Deposit Date | 2024-05-22 |
Published in |
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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 ... 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. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España Fondo Europeo de Desarrollo Regional (FEDER) Junta de Andalucía |
Project ID. | PID2019-106358GB-C21
PID2019-106358GB-C22 RYC-2017-22294 BES-2017-081561 P. R-S P18-FR-3531 P18-FR-644 US-1262867 US-1260906 |
Citation | Carmona, J.A., Rodríguez-Salamanca, P., Fernández Fernández, R.F., Lassaletta, J.M. y Hornillos, V. (2023). Dynamic kinetic resolution of 2-(Quinolin-8-yl)benzaldehydes: atroposelective iridium-catalyzed transfer hydrogenative allylation. Angewandte Chemie - International Edition, 62 (35), e202306981. https://doi.org/10.1002/anie.202306981. |
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