Unexpected reactivity of acetylenic ω-ketoesters toward TBAF and t-BuOK; new cascade reactions affording allene and oxetane derivatives

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2689-2691

  Wendling, Florence ^a   Miesch, Michel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

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ARTICLE;

EID: 0009932294     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016263v     Document Type: Article

References (23)

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4. (b) Miesch, M.; Wendung, F. Eur. J. Org. Chem. 2000, 20, 3381-3392 and references therein.
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6. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
7. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
8. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
9. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
10. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
11. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett, 1991, 32, 2135-2136. Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879-3882. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031-7032. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110. Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2111-2118.
12. It has to be noted that Fukumoto et al. studied the intramolecular reactivity of olefinic ω-ketoesters in order to obtain polycyclic ring systems fused to cyclobutanes: (a) Ihara, M.; Taniguchi, T.; Makita, K.; Tanako, M.; Ohnishi, M.; Taniguchi, N.; Fukumoto, K. J. Am. Chem. Soc. 1993, 115, 8107-8115.
13. (b) Ihara, M.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Synthesis 1995, 1405-1410. If we applied the reaction conditions developed by Fukumoto et al. to our acetylenic ω-ketoesters, the corresponding silyl enol ethers were quantitatively recovered. The length of the carbon chain between the carbonyl group and the acetylenic moiety was chosen after molecular models examination so that the intramolecular cyclization could take place. The influence of the chain's length is actually under investigation: Miesch, M.; Wendung, F. J. Org. Chem. submitted for publication.
14. (b) Ihara, M.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Synthesis 1995, 1405-1410. If we applied the reaction conditions developed by Fukumoto et al. to our acetylenic ω-ketoesters, the corresponding silyl enol ethers were quantitatively recovered. The length of the carbon chain between the carbonyl group and the acetylenic moiety was chosen after molecular models examination so that the intramolecular cyclization could take place. The influence of the chain's length is actually under investigation: Miesch, M.; Wendung, F. J. Org. Chem. submitted for publication.
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21. -). The spiro compound 15 and the allene derivative 16 were also obtained in the same ratio (1/9), but the reaction was more sluggish and the overall yield lower (50%).
22. For data concerning another alkylideneoxetane, see: Sakai, T., Katayama, T., Takeda, A. J. Org. Chem. 1981, 46, 2924-2931.
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