Domino Mukaiyama–Michael reactions in the synthesis of polycyclic systems

Good results were obtained in the Mukaiyama–Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2-cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl 6 as catalyst. A second Mukaiyama–Michael reaction of this new silyl enol ether wi...

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Veröffentlicht in:Tetrahedron 2006-02, Vol.62 (8), p.1717-1725
Hauptverfasser: Sarabèr, Florence C.E., Dratch, Svetlana, Bosselaar, Geke, Jansen, Ben J.M., de Groot, Aede
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Sprache:eng
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Zusammenfassung:Good results were obtained in the Mukaiyama–Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2-cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl 6 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. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.059