Intramolecular cyclization of conjugated diene and acetylene with (η2-propene)Ti(O-i-Pr)2. Generation and reaction of titanabicycles having an allyltitanium moiety

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1253-1256

  Urabe, Hirokazu ^a   Takeda, Tohru ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030020375     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02409-3     Document Type: Article

References (32)

1. For a most recent review: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259. See also literature cited in Ref 2.
2. Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261.
3. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203.
4. Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120. See note 25 in this literature.
5. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
6. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
7. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
8. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
9. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
10. Intramolecular cyclization of unsaturated compounds including conjugated diene with Ti and Zr species has not been addressed: see the following reviews. 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. Intermolecular reactions of a diene-zirconium complex with acetylene or olefin: Ref 4. Yasuda, H.; Nakamura, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Reactions of an olefin-or (strained) acetylene-zirconium complex with diene have also been reported: Negishi, E.; Miller, S. R. J. Org. Chem. 1989, 54, 6014. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441.
11. Other metal-catalyzed intramolecular cyclizations of conjugated diene and olefin (or acetylene), see: Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. Takacs, J. M.; Chandramouli, S. V. J. Org. Chem. 1993, 58, 7315. Takacs, J. M.; Boito, S. C. Tetrahedron Lett. 1995, 36, 2941, and references cited therein. Although the products are Diels-Alder-type compounds in the first two reports, such products were not observed in the present titanium-mediated reaction.
12. Other metal-catalyzed intramolecular cyclizations of conjugated diene and olefin (or acetylene), see: Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. Takacs, J. M.; Chandramouli, S. V. J. Org. Chem. 1993, 58, 7315. Takacs, J. M.; Boito, S. C. Tetrahedron Lett. 1995, 36, 2941, and references cited therein. Although the products are Diels-Alder-type compounds in the first two reports, such products were not observed in the present titanium-mediated reaction.
13. Other metal-catalyzed intramolecular cyclizations of conjugated diene and olefin (or acetylene), see: Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. Takacs, J. M.; Chandramouli, S. V. J. Org. Chem. 1993, 58, 7315. Takacs, J. M.; Boito, S. C. Tetrahedron Lett. 1995, 36, 2941, and references cited therein. Although the products are Diels-Alder-type compounds in the first two reports, such products were not observed in the present titanium-mediated reaction.
14. Other metal-catalyzed intramolecular cyclizations of conjugated diene and olefin (or acetylene), see: Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962. McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. Takacs, J. M.; Chandramouli, S. V. J. Org. Chem. 1993, 58, 7315. Takacs, J. M.; Boito, S. C. Tetrahedron Lett. 1995, 36, 2941, and references cited therein. Although the products are Diels-Alder-type compounds in the first two reports, such products were not observed in the present titanium-mediated reaction.
15. Although the exact nature of 5 is unclear, it is tentatively drawn as in a σ-allyl form and, accordingly, it may be the corresponding π-allyl structure.
16. 2)PO (R = H, Me) (Ukai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4029).
17. 2)PO (R = H, Me) (Ukai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4029).
18. 13C NMR spectroscopy.
19. It is interesting to compare the result of entry 4 in Table 1 with the following observation. The titanabicycle 23 (Ref 2) afforded the adduce 24 with Cyclohexanecarbaldehyde only in a low yield under similar reaction conditions and the reaction preferentially occurred at the alkenyl-Ti bond. (equation presented)
20. Transfer of an allyl group in titanium reagents to carbonyl compounds is one of the most feasible reactions: see, Reetz, M. T. In Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; p 116.
21. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
22. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
23. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
24. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
25. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
26. Among metallacycles of early transition metals, zirconacycles have been shown to react with a few carbon electrophiles, see: Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695. Gordon, G. J.; Whitby, R. J. Synlett 1995, 77. Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109. Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
27. Review on reactions of allyltitanium reagents: Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139 and other review articles cited therein. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
28. Review on reactions of allyltitanium reagents: Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 139 and other review articles cited therein. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
29. For our recent work on the generation and application of allyltitanium reagents, see: Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. Zubaidha, P. K.; Kasatkin, A.; Sato, F. J. Chem. Soc., Chem. Commun., in press.
30. For our recent work on the generation and application of allyltitanium reagents, see: Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. Zubaidha, P. K.; Kasatkin, A.; Sato, F. J. Chem. Soc., Chem. Commun., in press.
31. For our recent work on the generation and application of allyltitanium reagents, see: Urabe, H.; Yoshikawa, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5595. Kasalkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. Zubaidha, P. K.; Kasatkin, A.; Sato, F. J. Chem. Soc., Chem. Commun., in press.
32. A recent example of E selective preparation of homoallyl alcohols from an allylzirconocene derivative and carbonyl compounds: López, L.; Berlekamp, M.; Kowalski, D.; Erker, G. Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.