Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1217-1220

  Weibel, Douglas ^a,b   Gevorgyan, Vladimir ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000247652     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9717705     Document Type: Article

References (36)

1. Pellegrin, M. M. Rec. Trav. Chim. Pays-Bas 1899, 18, 457.
2. Brown, C. J.; Farthing, A. C. Nature 1949, 915, 915.
3. Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691.
4. For recent reviews see: (a) Topics Current Chemistry 172; Weber, E., Ed.; Springer-Verlag: Berlin, 1994. (b) Cyctophane Chemistry; Vögtle, F., Ed.; Willey: Chichester, 1993. (c) F. Diederich, Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
5. For recent reviews see: (a) Topics Current Chemistry 172; Weber, E., Ed.; Springer-Verlag: Berlin, 1994. (b) Cyctophane Chemistry; Vögtle, F., Ed.; Willey: Chichester, 1993. (c) F. Diederich, Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
6. For recent reviews see: (a) Topics Current Chemistry 172; Weber, E., Ed.; Springer-Verlag: Berlin, 1994. (b) Cyctophane Chemistry; Vögtle, F., Ed.; Willey: Chichester, 1993. (c) F. Diederich, Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
7. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
8. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
9. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
10. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
11. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
12. See for example: (a) Toyota, M.; Kinugawa, T.; Asakawa, Y. Photochemistry 1994, 37, 859. (b) Fukuyama, Y.; Asakawa, Y. Phytochemistry 1991, 30, 4061. (c) Hashimoto, T.; Kanayama, S.; Kan, Y.; Ton, M.; Asakawa, Y. Chem. Lett. 1996, 741. (d) Hashimoto, T.; Yoshida, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Tetrahedron Lett. 1994, 35, 909. (e) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett 1989, 30, 6043. (f) Sutherland, I. O. In Cyclophanes, Keehn, P. M., Rosenfeld, S. M., Eds.; Vol. II, p 602, Academic Press; New York, 1983. See also ref 4b, p 431.
13. See for example: (a) Heleson, R. C.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1974, 96, 7380. (b) Heleson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411. (c) Allwood, B. L.; Spencer, N.; Shahriari-Zavarech, H.; Stoddart, J. F. Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061. (d) Frensch, K.; Vögtle, F. J. Org. Chem. 1979, 44, 884. (e) Jarvi, E. T.; Whitlock, Jr. H. W. J. Am. Chem. Soc. 1980, 102, 657.
14. See for example: (a) Heleson, R. C.; Timko, J. M.; Cram, D. J. L.; Am. Chem. Soc. 1974, 96, 7380. (b) Heleson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411. (c) Allwood, B. L.; Spencer, N.; Shahriari-Zavarech, H.; Stoddart, J. F. Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061. (d) Frensch, K.; Vögtle, F. J. Org. Chem. 1979, 44, 884. (e) Jarvi, E. T.; Whitlock, Jr. H. W. J. Am. Chem. Soc. 1980, 102, 657.
15. See for example: (a) Heleson, R. C.; Timko, J. M.; Cram, D. J. L.; Am. Chem. Soc. 1974, 96, 7380. (b) Heleson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411. (c) Allwood, B. L.; Spencer, N.; Shahriari-Zavarech, H.; Stoddart, J. F. Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061. (d) Frensch, K.; Vögtle, F. J. Org. Chem. 1979, 44, 884. (e) Jarvi, E. T.; Whitlock, Jr. H. W. J. Am. Chem. Soc. 1980, 102, 657.
16. See for example: (a) Heleson, R. C.; Timko, J. M.; Cram, D. J. L.; Am. Chem. Soc. 1974, 96, 7380. (b) Heleson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411. (c) Allwood, B. L.; Spencer, N.; Shahriari-Zavarech, H.; Stoddart, J. F. Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061. (d) Frensch, K.; Vögtle, F. J. Org. Chem. 1979, 44, 884. (e) Jarvi, E. T.; Whitlock, Jr. H. W. J. Am. Chem. Soc. 1980, 102, 657.
17. See for example: (a) Heleson, R. C.; Timko, J. M.; Cram, D. J. L.; Am. Chem. Soc. 1974, 96, 7380. (b) Heleson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411. (c) Allwood, B. L.; Spencer, N.; Shahriari-Zavarech, H.; Stoddart, J. F. Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1061. (d) Frensch, K.; Vögtle, F. J. Org. Chem. 1979, 44, 884. (e) Jarvi, E. T.; Whitlock, Jr. H. W. J. Am. Chem. Soc. 1980, 102, 657.
18. For reviews see: (a) ref 4b p 447. (b) ref 4a p 87.
19. For reviews see: (a) ref 4b p 447. (b) ref 4a p 87.
20. For reviews see: (a) ref 4. See also for example: (b) Iyoda, M.; Sakaitani, M.; Otsuka, H.; Oda, M. Tetrahedron Lett. 1985, 26, 4777. (c) Shea, K. L.; Burke, L. D.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 5305. (d) See ref 6d.
21. For reviews see: (a) ref 4. See also for example: (b) Iyoda, M.; Sakaitani, M.; Otsuka, H.; Oda, M. Tetrahedron Lett. 1985, 26, 4777. (c) Shea, K. L.; Burke, L. D.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 5305. (d) See ref 6d.
22. For reviews see: (a) ref 4. See also for example: (b) Iyoda, M.; Sakaitani, M.; Otsuka, H.; Oda, M. Tetrahedron Lett. 1985, 26, 4777. (c) Shea, K. L.; Burke, L. D.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 5305. (d) See ref 6d.
23. For reviews see: (a) ref 4. See also for example: (b) Iyoda, M.; Sakaitani, M.; Otsuka, H.; Oda, M. Tetrahedron Lett. 1985, 26, 4777. (c) Shea, K. L.; Burke, L. D.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 5305. (d) See ref 6d.
24. Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042.
25. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970.
26. Ether cyclophanes having a vinyl group adjacent to a benzene ring are useful substrates for the synthesis of cyclobutane-linked crownophanes via a [2 + 2] photocycloaddition reaction. See: Inokuma, S.; Yamamoto, T.; Nishimura, J. Tetrahedron Lett 1990, 31, 97.
27. Klusener, P. A. A.; Kulik, W.; Brandsma, L. J. Org. Chem. 1987, 52, 5261.
28. It is generally accepted that alkylation of substrates bearing a β-alkoxy functionality is difficult due to the electron-withdrawing nature of the β-oxygen. For a review see: Streitwieser, A. Solvolytic Displacement Reactions; McGraw-Hill: New York, 1962; pp 16-18.
29. Direct nucleophilic alkylation at the carbon center of triflates bearing a β-oxygen atom has been reported. For a review on alkylations with organocuprate reagents see for example: (a) Lipshutz, B. H. Synthesis 1987, 325. For alkylations with Grignard reagents see: (b) Kotsuki, H.; Kadota, I.; Ochi, M. Tetrahedron Lett. 1989, 30, 1281.
30. Direct nucleophilic alkylation at the carbon center of triflates bearing a β-oxygen atom has been reported. For a review on alkylations with organocuprate reagents see for example: (a) Lipshutz, B. H. Synthesis 1987, 325. For alkylations with Grignard reagents see: (b) Kotsuki, H.; Kadota, I.; Ochi, M. Tetrahedron Lett. 1989, 30, 1281.
31. Kotsuki, H.; Kadota, I.; Ochi, M. Tetrahedron Lett. 1990, 31, 4609.
32. For regeoselective epoxide ring openings with acetylides in the presence of metal salts, see: Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1991, 32, 6617.
33. During the course of our studies on the palladium-catalyzed homo-benzannulation of conjugated enynes, we have found that addition of 3-10 equiv of phosphine ligand vs Pd allows a significant decrease in the amount of palladium catalyst used. Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. Unpublished results.
34. A template-directed effect of alkali metal salts in the ruthenium-catalyzed ring-closure metathesis has been recently demonstrated, see: Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101.
35. It is worth noting that in the intermolecular mode of the palladium-catalyzed homo-benzannulation of conjugated enynes, the palladium catalyst tolerates the presence of a hydroxy group. See: refs 10, 17.
36. It was also found that 2,4-disubstituted enynes do not undergo intermolecular homo-benzannulation under the mentioned reaction conditions. Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 35, 8603.