title: General, stereoselective synthesis of (Z)-beta,gamma-unsaturated nitriles promoted by samarium diiodide.
abstract: A method to obtain (Z)-beta,gamma-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with SmI2. The starting compounds were readily prepared, and a mechanism is proposed to explain this stereoselective beta-elimination reaction.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
authors.forename: José M
authors.initials: JM
authors.lastname: Concellón
authors.forename: Humberto
authors.initials: H
authors.lastname: Rodríguez-Solla
authors.forename: Carmen
authors.initials: C
authors.lastname: Simal
authors.forename: David
authors.initials: D
authors.lastname: Santos
authors.forename: Nieves R
authors.initials: NR
authors.lastname: Paz
mesh_terms: D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007454:Iodides; D009570:Nitriles; D012493:Samarium; C409809:samarium diiodide