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

Olga Konstantinova, Florence C.E. Sarabèr, Enrique Melguizo, Ben J.M. Jansen, Aede De Groot*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review


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 enol 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
Number of pages7
Issue number8
Publication statusPublished - 20 Feb 2006
MoE publication typeA1 Journal article-refereed


  • 1-Phenylthio-3-vinyl-cyclohex-1-en-3-ol
  • Addition
  • Bis-annelation
  • Silyl enol ethers


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