Repositorio de producción científica de la Universidad de Sevilla

Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

 

Advanced Search
 
Opened Access Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters
Cites

Show item statistics
Icon
Export to
Author: Carmona, José A.
Gonzalo Calvo, Gonzalo de
Serrano Vallez, Inmaculada
Crespo-Peña, Ana
Šimek, Michal
Monge Fernández, David
Fernández, Rafael
Lassaletta, José M.
Department: Universidad de Sevilla. Departamento de Química Orgánica
Date: 2017
Published in: Organic and Biomolecular Chemistry, 15, 2993-3005.
Document type: Article
Abstract: A series of peracylated glycosamine-derived thioureas have been synthesized and their 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 racemization-free tranformations of both aromatic- and aliphatic-substituted diazene products in a one pot fashion provide a direct entry to valuable azoxy compounds and α-hydroxy-β-amino esters.
Cite: Carmona, J.A., Gonzalo Calvo, G., Murcia Serrano, I., Crespo-Peña, A., Šimek, M., Monge, D.,...,Lassaletta, J.M. (2017). Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters. Organic and Biomolecular Chemistry, 15, 2993-3005.
Size: 1.139Mb
Format: PDF

URI: https://hdl.handle.net/11441/75103

DOI: 10.1039/c7ob00308k

See editor´s version

This work is under a Creative Commons License: 
Atribución-NoComercial-SinDerivadas 3.0 Estados Unidos de América

This item appears in the following Collection(s)