2024-03-28T15:52:01Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1487452021-10-01T11:10:12Zcom_10261_38com_10261_5col_10261_291
00925njm 22002777a 4500
dc
Carmona, José A.
author
Gonzalo, Gonzalo de
author
Serrano, Inmaculada
author
Crespo-Peña, Ana
author
Šimek, Michal
author
Fernández, Rosario
author
Lassaletta, José M.
author
2017
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
Organic and Biomolecular Chemistry, 15: 2993-3005 (2017)
http://hdl.handle.net/10261/148745
0.1039/C7OB00308K
Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α- hydroxy-β-amino esters