Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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A preparation of bicyclo[2.2.2]octan-2-one by sequential Michael reactions.

Machado, Shirley Muniz ; Silva, Felipe César Sousa e ; Silva, Gil Valdo José da ;

Abstract:

Bicyclo[2.2.2]octan-2-ones are efficient starting materials for the synthesis of natural products. Bicyclic compounds are traditionally synthesized through Diels Alder reactions; these bicyclo[2.2.2]octan-2-ones have been synthesized using cross-conjugate dienes derived from cyclohexenones. We report here some experimental results in which the bicyclic system was obtained by reaction of an enolate with methyl vinyl ketone, indicating that it could be the result of two sequential Michael additions.

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Palavras-chave: Michael reaction, 5, 5-dimethylcyclohex-2-enone, bicyclo[222]octan-2-one,

Palavras-chave: ,

DOI: 10.5151/chempro-14bmos-R0099-2

Referências bibliográficas
  • [1] 1 Little, R. D.; Masjedizadeh, M. R.; Wallquist, O. and McLoughlin, J. I.; Org. React., 1995, 47, 315.
  • [2] 2 a) Nozaki, H.; Yamaguti, T; Ueda, S. and Kondo, K. Tetrahedron, 1968, 24, 1445. b) Scott, J. W.; Vetter, W.; Oberhansli, W. E. and Fürst, A.; Tetrahedron Letters, 1972, 13, 1719.
  • [3] White, K. B. and Reusch, W.; Tetrahedron, 1978, 34, 2439.
  • [4] Gannon, W. F. and House, H. O.; Org. Synth, 1973, coll. vol. 5, 539.
  • [5] Bergman, R. e Magnusson, G.; J. Org. Chem., 1986, 51, 212-217.
Como citar:

Machado, Shirley Muniz; Silva, Felipe César Sousa e; Silva, Gil Valdo José da; "A preparation of bicyclo[2.2.2]octan-2-one by sequential Michael reactions.", p. 99 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0099-2

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