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Title

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.
URIhttp://hdl.handle.net/10261/156152
DOI10.1039/c7ob00308k
Identifiersdoi: 10.1039/c7ob00308k
issn: 1477-0520
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