1-phenylthio-3-vinyl-3-cyclohexenol, a new reagent for bis-annelation of silyl enol ethers

O. Konstantinova, F.C.E. Sarabèr, E. Melguizo, B.J.M. Jansen, Æ. de Groot

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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.
Original languageEnglish
Pages (from-to)1749-1755
JournalTetrahedron
Volume62
Issue number8
DOIs
Publication statusPublished - 2006

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Keywords

  • noyau cyclopentanonaphtalenique hydrogene
  • la synthese totale
  • d-homo-steroids
  • isoxazole annelation
  • vinyl ketones
  • efficient
  • vinylsilanes
  • sterolique
  • cetones

Cite this

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