English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/156152
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:


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

AuthorsCarmona, José A.; Gonzalo, Gonzalo de; Serrano, Inmaculada; Crespo-Peña, Ana; Šimek, Michal; Monge, David; Fernández, Rafael ; Lassaletta, José M.
Issue Date2017
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 15: 2993- 3005 (2017)
AbstractA 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.
Identifiersdoi: 10.1039/c7ob00308k
issn: 1477-0520
Appears in Collections:(IIQ) Artículos
Files in This Item:
File Description SizeFormat 
OB-ART-02-2017-000308 Revised (2).pdf1,17 MBAdobe PDFThumbnail
Show full item record
Review this work

Related articles:

WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.