Selective reaction of aldehydes with bicyclic titanacyclopentadienes or titanacyclopentenes prepared in Situ from 1,6- or 1,7-diynes or enynes and (η2-Propene)Ti(O-i-Pr)2

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6756-6757

  Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001693985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961340z     Document Type: Article

References (31)

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2. (b) Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163.
3. (c) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124 and other review articles cited therein.
4. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
5. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
6. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
7. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
8. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
9. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
10. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
11. 2-zirconacycles with heteroatom electrophiles are also possible; see: Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. Chem. Lett. 1992, 1693. Takahashi, T.; Aoyagi, K.; Hara, R.; Suzuki, N. J. Chem. Soc., Chem. Commun. 1993, 1042. Takahashi, T.; Aoyagi, K.; Kondakov, D. Y. J. Chem. Soc., Chem. Commun. 1994, 747. Mori, M.; Uesaka, N.; Saitoh, F.; Shibasaki, M. J. Org. Chem. 1994, 59, 5643.
12. Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695.
13. Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911.
14. Other methods for carbon-carbon bond formation based on metallacyclopentadienes of early transition metals have been reported. For ring closure with an olefin, acetylene, or nitrile, see ref 4. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361. Balaich, G. J.; Rothwell, I. P. Tetrahedron 1995, 57, 4463. For copper-promoted allylation, see: Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
15. Other methods for carbon-carbon bond formation based on metallacyclopentadienes of early transition metals have been reported. For ring closure with an olefin, acetylene, or nitrile, see ref 4. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361. Balaich, G. J.; Rothwell, I. P. Tetrahedron 1995, 57, 4463. For copper-promoted allylation, see: Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
16. Other methods for carbon-carbon bond formation based on metallacyclopentadienes of early transition metals have been reported. For ring closure with an olefin, acetylene, or nitrile, see ref 4. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361. Balaich, G. J.; Rothwell, I. P. Tetrahedron 1995, 57, 4463. For copper-promoted allylation, see: Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
17. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as 1,2-bis-anionic species; see: Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234. See also: Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
18. 4 and Grignard reagents was first reported by Kulinkovich et al. They utilized this complex as 1,2-bis-anionic species; see: Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234. See also: Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
19. 4 and i-PrMgCl as a divalent titanium reagent, see: Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
20. 4 and i-PrMgCl as a divalent titanium reagent, see: Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
21. 4 and i-PrMgCl as a divalent titanium reagent, see: Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
22. 4 and i-PrMgCl as a divalent titanium reagent, see: Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
23. (a) Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261.
24. (b) Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253.
25. The details are described in the supporting information.
26. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981.
27. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981.
28. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139.
29. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139.
30. 2-zirconacyclopentenes; see: Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Lipshutz, B. H.; Segi, M. Tetrahedron 1995, 51, 4407.
31. 2-zirconacyclopentenes; see: Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Lipshutz, B. H.; Segi, M. Tetrahedron 1995, 51, 4407.