Organometallic reactions in aqueous media: indium-promoted additions to 2-pyridyl and glyoxylic acid oxime ethers.
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
Luca
L
Dipartimento di Chimica Organica A. Mangini, Facoltà di Chimica Industriale, Università di Bologna, viale Risorgimento 4, 40136 Bologna, Italy.
Cerè
Vanda
V
Femoni
Cristina
C
Pollicino
Salvatore
S
Ricci
Alfredo
A