Iron(III)-induced tandem Nazarov cyclization-rearrangement of α-(trimethylsilylmethyl)divinyl ketone. Synthesis of the bicyclo[4.3.0]nonane ring system via spiro[4.4]nonane

Chemical Communications

Volumn , Issue 13, 1997, Pages 1177-1178

  Kuroda, Chiaki ^a   Sumiya, Hiroshi ^a   Murase, Atsushi ^a   Koito, Akira ^a  

^a RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542791585     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700816c     Document Type: Article

References (22)

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11. For examples, see C. Kuroda, S. Shimizu and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1990, 519; C. Kuroda, S. Inoue, R. Takemura and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, Bull. Chem. Soc. Jpn., 1996, 69, 2297; C. Kuroda, N. Mitsumata and C. Y. Tang, Bull. Chem. Soc. Jpn., 1996, 69, 1409.
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17. For related Nazarov cyclization of allylsilane derivatives, see S. E. Denmark, in Comprehensive Organic Synthesis, ed. B. M, Trost, Pergamon, Oxford, 1991, vol. 5, p. 751; S. E. Denmark and R. C. Klix, Tetrahedron, 1988, 44, 4043; S. E. Denmark, M. A. Wallace and C. B. Walker, Jr., J. Org. Chem., 1990, 55, 5543; K.-T. Kang, S. S. Kim, J. C. Lee and J. S. U, Tetrahedron Lett., 1992, 33, 3495.
18. For related Nazarov cyclization of allylsilane derivatives, see S. E. Denmark, in Comprehensive Organic Synthesis, ed. B. M, Trost, Pergamon, Oxford, 1991, vol. 5, p. 751; S. E. Denmark and R. C. Klix, Tetrahedron, 1988, 44, 4043; S. E. Denmark, M. A. Wallace and C. B. Walker, Jr., J. Org. Chem., 1990, 55, 5543; K.-T. Kang, S. S. Kim, J. C. Lee and J. S. U, Tetrahedron Lett., 1992, 33, 3495.
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22. For related type of ring formation, see W. L. Mock and M. E. Hartman, J. Org. Chem., 1977, 42, 459.