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Bifunctional Squaramide Organocatalysts for the Asymmetric Addition of Formaldehyde tert-Butylhydrazone to Simple Aldehydes
Author/s | Matador Martínez, Esteban
![]() ![]() ![]() ![]() ![]() ![]() de Gracia Retamosa, María Monge Fernández, David ![]() ![]() ![]() ![]() ![]() ![]() ![]() Iglesias Sigüenza, Francisco Javier ![]() ![]() ![]() ![]() ![]() ![]() ![]() Fernández Fernández, Rosario Fátima ![]() ![]() ![]() ![]() ![]() ![]() ![]() Lassaletta, José M. |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2018 |
Deposit Date | 2022-12-16 |
Published in |
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Awards | Premio Mensual Publicación Científica Destacada de la US. Facultad de Química |
Abstract | The nucleophilic addition of formaldehyde tert-butylhydrazone to simple aldehydes (a formal hetero-carbonyl–ene reaction) can be performed with good reactivity and excellent enantioselectivity by virtue of the dual ... The nucleophilic addition of formaldehyde tert-butylhydrazone to simple aldehydes (a formal hetero-carbonyl–ene reaction) can be performed with good reactivity and excellent enantioselectivity by virtue of the dual hydrogen-bonding activation exerted by amide–squaramide organocatalysts. The resulting hydroxydiazenes (azo alcohols) were isolated in high yields as enantiomerically enriched azoxy compounds after a regioselective azo-to-azoxy transformation. Subsequent derivatization provides an entry to relevant amino alcohols, oxazolidinones, and derivatives thereof. |
Funding agencies | Ministerio de Economía y Competitividad (MINECO). España Junta de Andalucía |
Project ID. | CTQ2016-76908-C2-1-P
![]() TQ2016-76908-C2-2-P ![]() 2012/FQM1078 ![]() |
Citation | Matador Martínez, E., de Gracia Retamosa, M., Monge Fernández, D., Iglesias Sigüenza, F.J., Fernández Fernández, R.F. y Lassaletta, J.M. (2018). Bifunctional Squaramide Organocatalysts for the Asymmetric Addition of Formaldehyde tert-Butylhydrazone to Simple Aldehydes. Chemistry - A European Journal, 24 (26), 6854-6860. https://doi.org/10.1002/chem.201801052. |
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