Artículo
Enantio- and Diastereoselective Nucleophilic Addition of N-tert-Butylhydrazones to Isoquinolinium Ions through Anion-Binding Catalysis
Autor/es | Matador Martínez, Esteban
Iglesias Sigüenza, Francisco Javier Monge Fernández, David Merino, Pedro Fernández Fernández, Rosario Fátima Lassaletta, J. M. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2021 |
Fecha de depósito | 2022-11-28 |
Publicado en |
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Premios | Premio Anual Publicación Científica Destacada de la US. Facultad de Química |
Resumen | 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. |
Agencias financiadoras | Ministerio de Ciencia, Innovación y Universidades (MICINN). España Gobierno de Aragón Junta de Andalucía |
Identificador del proyecto | PID2019-106358GB-C21
PID2019-106358GB-C22 PID2019-104090RB-100 E34_20R P18-FR-3531 P18-FR-644 US-1262867 |
Cita | 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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