Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 14, Pages 2993-3005Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00308k
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Funding
- Ministerio de Economia y Competitividad of Spain [CTQ2016-76908-C2-1-P, CTQ2016-76908-C2-2-P, RYC-2012-10014]
- European FEDER funds
- Junta de Andalucia [2012/FQM 1078]
- Universidad de Sevilla
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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 alpha-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-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 alpha-hydroxy-beta-amino esters.
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