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http://hdl.handle.net/10261/148745
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Título: | Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α- hydroxy-β-amino esters |
Autor: | Carmona, José A.; Gonzalo, Gonzalo de; Serrano, Inmaculada; Crespo-Peña, Ana; Šimek, Michal; Fernández, Rosario; Lassaletta, José M. ![]() |
Fecha de publicación: | 2017 |
Editor: | Royal Society of Chemistry (Great Britain) |
Citación: | Organic and Biomolecular Chemistry, 15: 2993-3005 (2017) |
Resumen: | A series of peracylated glycosamine-derived thioureas has been synthesized and its behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy- β-D-glucosamine derived 3,5-bis-(trifluoromethyl)phenyl thiourea the reaction could be accomplished with high yields (75- 98%) and moderate enantioselectivities (50-64% ee). Subsequent high-yielding and razemization-free tranformations of both aromatic- and aliphatic-substituted diazene products in one pot fashion provides a direct entry to valuable azoxy compounds and α-hydroxy-β-amino esters |
Versión del editor: | http://doi.org/10.1016/0.1039/C7OB00308K |
URI: | http://hdl.handle.net/10261/148745 |
DOI: | 0.1039/C7OB00308K |
Aparece en las colecciones: | (IIQ) Artículos |
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OB-ART-02-2017-000308 Revised.pdf | 1,17 MB | Adobe PDF | ![]() Visualizar/Abrir |
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