An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)5(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4463-4466

  Iwasawa, Nobuharu ^a   Miura, Tomoya ^a   Kiyota, Koichi ^a   Kusama, Hiroyuki ^a   Lee, Kooyeon ^b   Lee, Phil Ho ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Kangwon National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0013231813     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026993i     Document Type: Article

References (37)

1. For a review on the cyclopentene annulation, see: (a) Ramaiah, M. Synthesis 1984, 529. (b) Trost. B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
2. For a review on the cyclopentene annulation, see: (a) Ramaiah, M. Synthesis 1984, 529. (b) Trost. B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
3. For recent examples of cyclopentannulation see: (a) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. (b) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2002, 124, 5948. (d) Ding, P.; Ghosez, L. Tetrahedron 2002, 58, 1565. (e) Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron 2002, 58, 6991 and references therein.
4. For recent examples of cyclopentannulation see: (a) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. (b) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2002, 124, 5948. (d) Ding, P.; Ghosez, L. Tetrahedron 2002, 58, 1565. (e) Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron 2002, 58, 6991 and references therein.
5. For recent examples of cyclopentannulation see: (a) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. (b) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2002, 124, 5948. (d) Ding, P.; Ghosez, L. Tetrahedron 2002, 58, 1565. (e) Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron 2002, 58, 6991 and references therein.
6. For recent examples of cyclopentannulation see: (a) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. (b) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2002, 124, 5948. (d) Ding, P.; Ghosez, L. Tetrahedron 2002, 58, 1565. (e) Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron 2002, 58, 6991 and references therein.
7. For recent examples of cyclopentannulation see: (a) Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. (b) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (c) Barluenga, J.; Martínez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2002, 124, 5948. (d) Ding, P.; Ghosez, L. Tetrahedron 2002, 58, 1565. (e) Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron 2002, 58, 6991 and references therein.
8. (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604.
9. (b) Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935.
10. (c) Danheiser, R. L.; Fink, D. M.; Tsai, Y.-M. Org. Synth. 1988, 66, 8. See also: Panek, S. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 596-607.
11. (c) Danheiser, R. L.; Fink, D. M.; Tsai, Y.-M. Org. Synth. 1988, 66, 8. See also: Panek, S. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 596-607.
12. (a) Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928.
13. (b) Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871.
14. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
15. 5(L)-promoted reactions cited therein.
16. See also: (e) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4081.
17. (f) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Sudo, T.; Asao, N.; Yamamoto, Y. Can. J. Chem. 2001, 79, 1624.
18. Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions were reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuda, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han. Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
19. Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions were reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuda, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han. Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
20. Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions were reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuda, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han. Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
21. Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions were reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuda, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han. Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
22. 5 and a silyl chloride such as TMSCl or TBSCl, only hydrolyzed conjugate adduct was obtained and none of the desired silyl enol ether was detected in the crude mixtures.
23. Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3025.
24. For examples of In-mediated propargylation or allenylation, see: (a) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472. (c) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003.
25. For examples of In-mediated propargylation or allenylation, see: (a) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472. (c) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003.
26. For examples of In-mediated propargylation or allenylation, see: (a) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472. (c) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003.
27. 5 π-complex and the vinylidene complex: the ratio of two reaction pathways is about 7:3 (π-complex vs vinylidene complex) for 2d. (10) Stereochemistry of the ring junction is assigned as cis by a NOE experiment; for details, see Supporting Information.
28. Products 3a-f were accompanied by a small amount (about 3% of the product) of an olefinic regioisomer such as 3a′. The reason for the formation of this compound is not yet obvious. (Matrix Presented)
29. (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
30. (b) Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976. 736.
31. 4a see: (a) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691. (b) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071. See also: (d) Amrein, S.; Studer, A. Chem. Commun. 2002, 1592. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
32. 4a see: (a) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691. (b) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071. See also: (d) Amrein, S.; Studer, A. Chem. Commun. 2002, 1592. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
33. 4a see: (a) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691. (b) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071. See also: (d) Amrein, S.; Studer, A. Chem. Commun. 2002, 1592. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
34. 4a see: (a) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691. (b) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071. See also: (d) Amrein, S.; Studer, A. Chem. Commun. 2002, 1592. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
35. 4a see: (a) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691. (b) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339. (c) Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071. See also: (d) Amrein, S.; Studer, A. Chem. Commun. 2002, 1592. (e) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492.
36. 5(amine) complex; see: Kirtley, S. W. In Comprehensive Organometallics Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergamon Press: Oxford, UK, 1982; Vol. 3, p 1079.
37. Isolated products 4a, 4e, and 4f were gradually isomerized to the bicyclo[4.3.0]nona-1,8-diene derivatives.