Oxime ethers derived from 2-pyridinecarboxaldehyde and glyoxylic acid can be effectively allylated in water with five differently functionalized allylic bromides promoted by indium. When the metal is positioned in close proximity of flanking heteroatomic centers, chelation by In is indeed operative and affects both reactivity and stereochemistry. Stereochemical assignments in the addition products were based on X-ray crystallographic measurements and spectral correlations.
Bernardi, L., Cere, V., Femoni, C., Pollicino, S., Ricci, A. (2003). Organometallic reactions in aqueous media: Indium-promoted additions to 2-pyridyl and glyoxylic acid oxime ethers. JOURNAL OF ORGANIC CHEMISTRY, 68(8), 3348-3351 [10.1021/jo026823j].
Organometallic reactions in aqueous media: Indium-promoted additions to 2-pyridyl and glyoxylic acid oxime ethers
Bernardi L.;Femoni C.;Pollicino S.;Ricci A.
2003
Abstract
Oxime ethers derived from 2-pyridinecarboxaldehyde and glyoxylic acid can be effectively allylated in water with five differently functionalized allylic bromides promoted by indium. When the metal is positioned in close proximity of flanking heteroatomic centers, chelation by In is indeed operative and affects both reactivity and stereochemistry. Stereochemical assignments in the addition products were based on X-ray crystallographic measurements and spectral correlations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
