A novel tandem cyclization of 2,7- or 2,8-bis-unsaturated esters mediated by (η2-propene)TiX2 (X = Cl or O-i-Pr). A facile construction of bicyclo[3.3.0]octane, -[4.3.0]nonane, and -[3.1.0]hexane skeletons

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8729-8730

  Suzuki, Ken ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[3.3.0]OCTANE DERIVATIVE; BICYCLO[4.3.0]NONANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029823460     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961928n     Document Type: Article

References (41)

1. (a) Urabe, H.; Hata, T.; Sato. F. Tetrahedron Lett. 1995, 36. 4261.
2. (b) Urabe. H.; Takeda. T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253.
3. 2Ti complexes has not been mentioned before; see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. See also: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
4. 2Ti complexes has not been mentioned before; see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. See also: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
5. 2Ti complexes has not been mentioned before; see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. See also: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
6. 2Ti complexes has not been mentioned before; see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. See also: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
7. Preparation of bicyclic ketone(or imine) - zirconium complexes via zirconium-mediated cyclization and carbonylation of dienes and enynes was reported; see: Probert, G. D.; Whitby. R. J.; Coote, S. J. Tetrahedron Lett. 1995, 36,4113. Barluenga, J.; Sanz, R.; Fañanás, F. J. J. Chem. Soc., Chem. Commun. 1995, 1009
8. Preparation of bicyclic ketone(or imine) - zirconium complexes via zirconium-mediated cyclization and carbonylation of dienes and enynes was reported; see: Probert, G. D.; Whitby. R. J.; Coote, S. J. Tetrahedron Lett. 1995, 36,4113. Barluenga, J.; Sanz, R.; Fañanás, F. J. J. Chem. Soc., Chem. Commun. 1995, 1009
9. 4 gave somewhat better results in the reactions of type I and II. For choice of these titanium salts in a few relevant reactions, see: Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. Kasatkin, A.; Nakagawa, T.; Okamoto, S.: Sato, F. J. Am. Chem. Soc: 1995, 117. 3881. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
10. 4 gave somewhat better results in the reactions of type I and II. For choice of these titanium salts in a few relevant reactions, see: Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. Kasatkin, A.; Nakagawa, T.; Okamoto, S.: Sato, F. J. Am. Chem. Soc: 1995, 117. 3881. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
11. 4 gave somewhat better results in the reactions of type I and II. For choice of these titanium salts in a few relevant reactions, see: Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. Kasatkin, A.; Nakagawa, T.; Okamoto, S.: Sato, F. J. Am. Chem. Soc: 1995, 117. 3881. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
12. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989. III. 3336.
13. Although the structure of 3 is tentatively drawn as in a C-Ti form, its exact nature is unknown, and accordingly, it may be the corresponding titanium enolate.
14. For the general reactivity of carbon - titanium bonds, see: Reetz, M. T. In Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin. 1986; p 116.
15. 2-zirconacycles with electrophiles, see: Aoyagi, K.; Kasai, K.; Kondakov, D. Y.: Hara, R.; Suzuki, N.; Takahashi, T. Inorg. Chim. Acta 1994, 220, 319. Mori. M.: Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994. 59, 5643.
16. 2-zirconacycles with electrophiles, see: Aoyagi, K.; Kasai, K.; Kondakov, D. Y.: Hara, R.; Suzuki, N.; Takahashi, T. Inorg. Chim. Acta 1994, 220, 319. Mori. M.: Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994. 59, 5643.
17. Experimental details are described in supporting information.
18. Cf.: Negishi, E.; Choueiry. D.: Nguyen, T. B.; Swanson. D. R J. Am. Chem. Soc: 1994, 116. 9751.
19. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
20. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
21. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
22. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
23. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
24. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
25. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
26. 2Ti complex, see ref Ia. With Rh complex, see: Matsuda. I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241. With Ni complex, see: Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110. 1286.
27. A similar flow of electrons is described in the isomerization of palladacyclopentenes to cyclopropylalkylidene - Pd complex; see: Trost, B. M.; Hashmi, S. K. J. Am. Chem. Soc. 1994, 116, 2183.
28. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
29. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
30. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
31. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
32. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
33. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
34. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
35. The presence of a titanium - carbene complex is invoked in several synthetic reactions; see: Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611. Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270. Yoshida, T.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 1276. Hartner, F. W.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293. Clawson, L.; Buchwald, S. L.; Grubbs, R. H. Tetrahedron Lett. 1984, 25, 5733. Okazoe, T.; Takai. K.; Oshima, K. Utimoto. K. J. Org. Chem. 1987, 52. 4410. Takai. K.: Fujimura, O.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 211.
36. Some compounds of a similar structure were characterized or have even found applications in organic synthesis; see: Poise, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 5393. Lee, S. Y.; Bergman, R. G. Tetrahedron 1995.51,4255. McGrane. P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
37. Some compounds of a similar structure were characterized or have even found applications in organic synthesis; see: Poise, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 5393. Lee, S. Y.; Bergman, R. G. Tetrahedron 1995.51,4255. McGrane. P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
38. Some compounds of a similar structure were characterized or have even found applications in organic synthesis; see: Poise, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 5393. Lee, S. Y.; Bergman, R. G. Tetrahedron 1995.51,4255. McGrane. P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
39. Cyclization of enynes with certain metal-carbene complexes afforded a similar class of compounds. However, a metallic moiety is not involved in the products, which is again in marked contrast to the reaction reported herein. For these reactions and also some synthetic utility of the products, see: Katz, T. J.; Yang, G. X.-Q. Tetrahedron Lett. 1991, 32, 5895. Mori, M.; Watanuki. S. J. Chem. Soc., Chem. Commun. 1992. 1082. Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61. 2268.
40. Cyclization of enynes with certain metal-carbene complexes afforded a similar class of compounds. However, a metallic moiety is not involved in the products, which is again in marked contrast to the reaction reported herein. For these reactions and also some synthetic utility of the products, see: Katz, T. J.; Yang, G. X.-Q. Tetrahedron Lett. 1991, 32, 5895. Mori, M.; Watanuki. S. J. Chem. Soc., Chem. Commun. 1992. 1082. Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61. 2268.
41. Cyclization of enynes with certain metal-carbene complexes afforded a similar class of compounds. However, a metallic moiety is not involved in the products, which is again in marked contrast to the reaction reported herein. For these reactions and also some synthetic utility of the products, see: Katz, T. J.; Yang, G. X.-Q. Tetrahedron Lett. 1991, 32, 5895. Mori, M.; Watanuki. S. J. Chem. Soc., Chem. Commun. 1992. 1082. Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61. 2268.