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Enantio- and Diastereoselective Nucleophilic Addition of N-tert-Butylhydrazones to Isoquinolinium Ions through Anion-Binding Catalysis
Author/s | Matador Martínez, Esteban
![]() ![]() ![]() ![]() ![]() ![]() Iglesias Sigüenza, Francisco Javier ![]() ![]() ![]() ![]() ![]() ![]() ![]() Monge Fernández, David ![]() ![]() ![]() ![]() ![]() ![]() ![]() Merino, Pedro Fernández Fernández, Rosario Fátima ![]() ![]() ![]() ![]() ![]() ![]() ![]() Lassaletta, J. M. |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2021 |
Deposit Date | 2022-11-28 |
Published in |
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Awards | Premio Anual Publicación Científica Destacada de la US. Facultad de Química |
Abstract | A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines employing N-tert-butylhydrazones as neutral α-azo carbanions and masked acyl anion equivalents has been developed. Experimental ... A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines employing N-tert-butylhydrazones as neutral α-azo carbanions and masked acyl anion equivalents has been developed. Experimental and computational data supports the generation of highly ordered complexes wherein the chloride behaves as a template for the catalyst, the hydrazone reagent, and the isoquinolinium cation, providing excellent stereocontrol in the formation of two contiguous stereogenic centers. The ensuing selective and high-yielding transformations provide appealing dihydroisoquinoline derivatives. |
Funding agencies | Ministerio de Ciencia, Innovación y Universidades (MICINN). España Gobierno de Aragón Junta de Andalucía |
Project ID. | PID2019-106358GB-C21
![]() PID2019-106358GB-C22 ![]() PID2019-104090RB-100 ![]() E34_20R ![]() P18-FR-3531 ![]() P18-FR-644 ![]() US-1262867 ![]() |
Citation | Matador Martínez, E., Iglesias Sigüenza, F.J., Monge Fernández, D., Merino, P., Fernández Fernández, R.F. y Lassaletta, J.M. (2021). Enantio- and Diastereoselective Nucleophilic Addition of N-tert-Butylhydrazones to Isoquinolinium Ions through Anion-Binding Catalysis. Angewandte Chemie - International Edition, 60 (10), 5096-5101. https://doi.org/10.1002/anie.202012861. |
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