Artículo
Asymmetric Organocatalytic Synthesis of Fluorinated β-Hydroxy Diazenes
Autor/es | Matador Martínez, Esteban
de Gracia Retamosa, María Jiménez Sánchez, Antonio Monge Fernández, David Fernández Fernández, Rosario Fátima Lassaletta, José M. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2019 |
Fecha de depósito | 2022-12-16 |
Publicado en |
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Resumen | The nucleophilic addition of formaldehyde tert-butyl hydrazone to fluoromethyl ketones provides a valuable tool for the synthesis of highly functionalized β-hydroxy β-tri- and difluoromethyl diazenes. Excellent reactivities ... The nucleophilic addition of formaldehyde tert-butyl hydrazone to fluoromethyl ketones provides a valuable tool for the synthesis of highly functionalized β-hydroxy β-tri- and difluoromethyl diazenes. Excellent reactivities and moderate to good enantioselectivities (up to 90 % ee) were achieved by H-bonding activation exerted by tert-Leucine derived H-bonding (squaramide or thiourea) organocatalysts. Subsequent derivatizations in one-pot fashion provide synthetically useful intermediates for target-oriented synthesis: tri- and di-fluoromethylated azoxy compounds, β-amino alcohols, α-hydroxy aldoximes and derivatives thereof. |
Agencias financiadoras | Ministerio de Economía y Competitividad (MINECO). España Junta de Andalucía |
Identificador del proyecto | CTQ2016-76908-C2-1-P
CTQ2016-76908-C2-2-P 2012/FQM1078 |
Cita | Matador Martínez, E., de Gracia Retamosa, M., Jiménez Sánchez, A., Monge Fernández, D., Fernández Fernández, R.F. y Lassaletta, J.M. (2019). Asymmetric Organocatalytic Synthesis of Fluorinated β-Hydroxy Diazenes. European Journal of Organic Chemistry, 2019 (1), 130-138. https://doi.org/10.1002/ejoc.201801477. |
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