Tandem cyclization of alkynylmetals bearing a remote leaving group via cycloalkylidene carbenes

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1855-1857

  Harada, Toshiro ^a   Fujiwara, Takayuki ^a   Iwazaki, Katsuhiro ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004461902     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0059145     Document Type: Article

References (28)

1. (a) Stang, P. J. Chem. Rev. 1978, 78, 383.
2. (b) Kirmse W. Angew. Chem. Int. Ed. Engl. 1997, 36, 1164.
3. (c) Taber, D. F. Methods of Organic Chemistry (Hauben Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, New York, 1995; Vol. E21a, p 1127.
4. (a) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081 and references therein.
5. (b) Taber, D. F.; Yu, H.; Incarvito, C. D.; Rheingold, A. L. J. Am. Chem. Soc. 1998, 120, 13285.
6. (c) Taber, D. F.; Christos, T. E.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1999, 121, 5589.
7. For review, see: (a) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274.
8. (b) Ochiai, M. Reviews on Heteroatom Chemistry, Volume 2; Oae, S., Ed.; MYU: Tokyo, 1989; p 92.
9. (a) Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281.
10. (b) Ochiai, M.; Kunishima M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144.
11. (c) Ochiai, M.; Ito T.; Takaoka, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118.
12. (d) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
13. (a) Kitamura, T.; Stang, P. J. Tetrahedron Lett. 1988, 29, 1887.
14. (b) Tykwinski, R. R.; Whiteford, J. A.; Stang, P. J. J. Chem. Soc., Chem. Commun. 1993, 1800.
15. (c) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93.
16. (d) Tykwinski, R. R.; Stang, P. J., Peisky N. E. Tetrahedron Lett. 1994, 35, 23.
17. (e) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
18. (a) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
19. (b) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
20. (c) Feldman, K. S.; Bruendl, M. M. Tetrahedron Lett. 1998, 39, 2911.
21. For a different approach, see ref 5d.
22. Harada, T.; Iwazaki, K.; Otani, T. Oku, A. J. Org. Chem. 1998, 63, 9007.
23. Johnson, W. S.; Elliott, R.; Elliot, D. J. J. Am. Chem. Soc. 1983, 105, 2904.
24. 2, THF, then NaOOH; 41%).
25. 2-(dppf), THF) gave (E)-3-(phenylmethylidene)-2-(2-phenylethyl)tetrahydrofuran (87%), whose E-geometry was determined by an NOE experiment.
26. The stereochemistry of the major isomer was established by NOE.
27. 16O: C, 83.96; H, 7.99. Found: C, 83.67; H, 7.93.
28. Brandsma, L.; Verkruijsse, H. D. Syntheses of Acetylenes, Allenes, and Cumulenes; Elsevier: Amsterdam, 1980; p 48.