IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Thermodynamically driven, syn-selective vinylogous aldol reaction of tetronamides
Autor/es:
ACOSTA, J.A.M.; KARAK, M.; SAROTTI, A.M.; BARBOSA, L.C.A.* ; BOUKOUVALAS, J.
Revista:
ORGANIC & BIOMOLECULAR CHEMISTRY
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: CAMBRIDGE; Año: 2016 vol. 14 p. 4897 - 4907
ISSN:
1477-0520
Resumen:
A stereoselective vinylogous aldol reaction of N-monosubstituted tetronamides with aldehydes is described. The procedure is simple and scalable, works well with both aromatic and aliphatic aldehydes, and affords mainly the corresponding syn-aldol adducts. In many cases, the latter are obtained essentially free of their anti-isomers (dr > 99 : 1) in high yields (70?90%). Experimental and computational studies suggest that the observed diastereoselectivity arises through anti?syn isomer interconversion, enabled by an iterative retro-aldol/aldol reaction.
