Addition reaction of vinylic reagents, derived from alpha-chloroenones, to carbonyl compounds promoted by samarium diiodide.
A new samarium diiodide-promoted addition reaction of vinylsamarium reagents, derived from (Z)-alpha-chloro-alpha,beta-unsaturated phenones 1, to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-unsaturated ketones in good yield. These transformations took place with total or very high inversion of the stereochemistry of the C-C double bond of the starting chloroenone, producing the Z diastereoisomer. A new methodology to prepare SmI(2) in acetonitrile by sonic treatment of 1,2-diiodoethane with Sm powder is also described. A mechanism to explain this transformation is proposed.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.se
Bernad
Pablo L
PL
Huerta
Mónica
M
García-Granda
Santiago
S
Díaz
M Rosario
MR