1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol (2) has been synthesized and investigated as a new bis-annelation reagent for silyl enol ethers. Reagent 2 can be synthesized by a Grignard reaction of vinyl magnesium bromide with 3-phenylthiocyclohexenone. The reaction with silyl cool ethers takes place Under Lewis acid catalysis and generally proceeds in good yields. The resulting phenylthiodienes can be hydrolyzed to enones, which have been cyclized in a homologous aldol reaction to polycyclic compounds.
- noyau cyclopentanonaphtalenique hydrogene
- la synthese totale
- isoxazole annelation
- vinyl ketones
Konstantinova, O., Sarabèr, F. C. E., Melguizo, E., Jansen, B. J. M., & de Groot, Æ. (2006). 1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers. Tetrahedron, 62(8), 1749-1755. https://doi.org/10.1016/j.tet.2005.11.060