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In the presence of a catalytic amount of lithium amide, the reaction of oxophorone with electron-deficient olefins afforded bicyclo[2.2.2]octane-2,5-dione derivatives in high yields. The reaction proceeds autocatalytically by an enolate of bicyclo[2.2.2]octane-2,5-dione, generated by an initial domino Michael reaction.

Metathesis reactionsMetathesis reactions O 0286 Domino Ring Opening-Ring Closing Metathesis (ROM-RCM) Strategy Toward Bicyclo[n.3.0]cycloalkenes. -This offers a convenient approach to bicyclo[3.3.0]octenes and bicyclo[4.3.0]nonenes, cis-and trans-fused systems are available. Protection of the OH group is necessary for successful reaction. Starting from the acrylate (VIII), only ring-opening metathesis takes place yielding the triene (IX). -(HAGIWARA*, H.; KATSUMI, T.; ENDOU, S.; HOSHI, T.; SUZUKI, T.; Tetrahedron 58 (2002) 33, 6651-6654; Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan; Eng.) -Jannicke 01-053

Bridged compoundsBridged compounds Q 0060 Autocatalytic Domino Michael Reaction Leading to Bicyclo[2.2.2]octane--2,5-dione Derivatives. -The title reaction is demonstrated for the first time. -(HAGIWARA*, H.; ENDOU, S.; FUKUSHIMA, M.; HOSHI, T.; SUZUKI, T.; Org. Lett. 6 (2004) 7, 1115-1118; Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan; Eng.) -Steudel 33-092

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