Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems

F.C.E. Sarabèr, S. Dratch, G. Bosselaar, B.J.M. Jansen, Æ. de Groot

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17 Citations (Scopus)

Abstract

Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated.
Original languageEnglish
Pages (from-to)1717-1725
JournalTetrahedron
Volume62
Issue number8
DOIs
Publication statusPublished - 2006

Keywords

  • silyl enol ethers
  • catalyzed conjugate addition
  • vitamin-d-3 northern portion
  • ring closure reactions
  • one-pot
  • acyclic stereoselection
  • titanium tetrachloride
  • 2+2+2 construction
  • carbonyl-compounds
  • organic-synthesis

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    Sarabèr, F. C. E., Dratch, S., Bosselaar, G., Jansen, B. J. M., & de Groot, Æ. (2006). Domino Mukaiyama-Michael reactions in the synthesis of polycyclic systems. Tetrahedron, 62(8), 1717-1725. https://doi.org/10.1016/j.tet.2005.11.059