A highly regioselective ring-opening metathesis-cross metathesis process modulated by the electronic effects of the cross metathesis partner: an entry to quaternary prolines.
A modulation of the regioselectivity in the ring-opening metathesis-cross metathesis (ROCM) process, originated by the electronic features of the acyclic olefin, is described. Electron-poor and electron-rich olefins showed opposing behavior giving different regioisomers. The reaction opens the way to the synthesis of interesting proline analogues incorporating a quaternary stereocenter.
Carreras
Javier
J
Departamento de Química, Universidad de La Rioja, Grupo de Sííntesis Química de La Rioja, UA-CSIC, 26006 Logrono, Spain.
Avenoza
Alberto
A
Busto
Jesús H
JH
Peregrina
Jesús M
JM
D000475:Alkenes / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004583:Electrons; D011392:Proline / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D002264:Carboxylic Acids; D011392:Proline