General, stereoselective synthesis of (Z)-beta,gamma-unsaturated nitriles promoted by samarium diiodide.
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.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Rodríguez-Solla
Humberto
H
Simal
Carmen
C
Santos
David
D
Paz
Nieves R
NR
D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
D007454:Iodides; D009570:Nitriles; D012493:Samarium; C409809:samarium diiodide