A novel [5+2] cycloaddition reaction using a dicobalt acetylene complex [6]

Journal of the American Chemical Society

Volumn 122, Issue 25, 2000, Pages 6116-6117

  Tanino, Keiji ^a   Shimizu, Tadashi ^b   Miyama, Motoki ^b   Kuwajima, Isao ^c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; CYCLOHEPTANE DERIVATIVE;

COMPLEX FORMATION; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034725388     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001003e     Document Type: Letter

References (39)

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4. For reviews of [4+3] cycloaddition reactions, see: (a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-19. (c) Mann, J. Tetrahedron 1986, 42, 4611-4659. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Harmata, M. Tetrahedron 1997, 53, 6235- 6280.
5. For reviews of [4+3] cycloaddition reactions, see: (a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-19. (c) Mann, J. Tetrahedron 1986, 42, 4611-4659. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Harmata, M. Tetrahedron 1997, 53, 6235- 6280.
6. For reviews of [4+3] cycloaddition reactions, see: (a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-19. (c) Mann, J. Tetrahedron 1986, 42, 4611-4659. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Harmata, M. Tetrahedron 1997, 53, 6235- 6280.
7. For reviews of [4+3] cycloaddition reactions, see: (a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-19. (c) Mann, J. Tetrahedron 1986, 42, 4611-4659. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Harmata, M. Tetrahedron 1997, 53, 6235- 6280.
8. For reviews of [4+3] cycloaddition reactions, see: (a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 5.1, pp 593-615. (b) Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1-19. (c) Mann, J. Tetrahedron 1986, 42, 4611-4659. (d) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163-344. (e) Harmata, M. Tetrahedron 1997, 53, 6235-6280.
9. For metal-catalized [5+2] cycloaddition reactions, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. (b) Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349 and references therein.
10. For metal-catalized [5+2] cycloaddition reactions, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. (b) Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349 and references therein.
11. For oxidopyrylium cycloadditions, see: (a) Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109-114. (b) West, F. In Advances in Cycloaddition; Lautens, M., Ed.; JAI Press: Greenwich, 1997; Vol. 4, pp 1-40. (c) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1997, 33, 2115-2118 and references therein.
12. For oxidopyrylium cycloadditions, see: (a) Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109-114. (b) West, F. In Advances in Cycloaddition; Lautens, M., Ed.; JAI Press: Greenwich, 1997; Vol. 4, pp 1-40. (c) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1997, 33, 2115-2118 and references therein.
13. For oxidopyrylium cycloadditions, see: (a) Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109-114. (b) West, F. In Advances in Cycloaddition; Lautens, M., Ed.; JAI Press: Greenwich, 1997; Vol. 4, pp 1-40. (c) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1997, 33, 2115-2118 and references therein.
14. Stepwise cycloaddition reactions of "allylsilane-acetal bifunctional reagents" with enol silyl ethers including [5+2]-type annulation were reported: (a) Lee, T. V.; Boucher, R. J.; Rockell, C. J. M. Tetrahedron Lett. 1988, 29, 689-692. (b) Lee, T. V.; Boucher, R. J.; Porter, J. R.; Rockell, C. J. M. Tetrahedron 1989, 45, 5887-5894. (c) Lee, T. V.; Cregg, C. Synlett 1990, 317-319.
15. Stepwise cycloaddition reactions of "allylsilane-acetal bifunctional reagents" with enol silyl ethers including [5+2]-type annulation were reported: (a) Lee, T. V.; Boucher, R. J.; Rockell, C. J. M. Tetrahedron Lett. 1988, 29, 689-692. (b) Lee, T. V.; Boucher, R. J.; Porter, J. R.; Rockell, C. J. M. Tetrahedron 1989, 45, 5887-5894. (c) Lee, T. V.; Cregg, C. Synlett 1990, 317-319.
16. Stepwise cycloaddition reactions of "allylsilane-acetal bifunctional reagents" with enol silyl ethers including [5+2]-type annulation were reported: (a) Lee, T. V.; Boucher, R. J.; Rockell, C. J. M. Tetrahedron Lett. 1988, 29, 689-692. (b) Lee, T. V.; Boucher, R. J.; Porter, J. R.; Rockell, C. J. M. Tetrahedron 1989, 45, 5887-5894. (c) Lee, T. V.; Cregg, C. Synlett 1990, 317-319.
17. (a) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946.
18. (b) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 1724-1731.
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20. Habermas, K. L.; Denmark, S. E. Org. React. 1994, 45, 1-158.
21. For examples, see: (a) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957. (b) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898. (d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
22. For examples, see: (a) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957. (b) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898. (d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
23. For examples, see: (a) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957. (b) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898. (d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
24. For examples, see: (a) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957. (b) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898. (d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
25. Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1997, 62, 3032-3033.
26. Cotton, F. A.; Jamerson, J. D.; Stults, B. R. J. Am. Chem. Soc. 1976, 98, 1774-1779.
27. For selected examples of seven-membered dicobalt acetylene complexs, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509- 2520. (c) Brook, M. A.; Urschey, J.; Stradiotto, M. Organometallics 1998, 17, 5342-5346. (d) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509- 510. (e) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
28. For selected examples of seven-membered dicobalt acetylene complexs, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509-2520. (c) Brook, M. A.; Urschey, J.; Stradiotto, M. Organometallics 1998, 17, 5342-5346. (d) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509- 510. (e) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
29. For selected examples of seven-membered dicobalt acetylene complexs, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509- 2520. (c) Brook, M. A.; Urschey, J.; Stradiotto, M. Organometallics 1998, 17, 5342-5346. (d) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509- 510. (e) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
30. For selected examples of seven-membered dicobalt acetylene complexs, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509- 2520. (c) Brook, M. A.; Urschey, J.; Stradiotto, M. Organometallics 1998, 17, 5342-5346. (d) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509-510. (e) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
31. For selected examples of seven-membered dicobalt acetylene complexs, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Yenjai, C.; Isobe, M. Tetrahedron 1998, 54, 2509- 2520. (c) Brook, M. A.; Urschey, J.; Stradiotto, M. Organometallics 1998, 17, 5342-5346. (d) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509- 510. (e) Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951-7952.
32. For reviews of synthetic utility of cobalt-complexed propargyl cations, see: (a) Nicholas, K. M. Acc. Chem. Res. 1987,20, 207-214. (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 685-702.
33. For reviews of synthetic utility of cobalt-complexed propargyl cations, see: (a) Nicholas, K. M. Acc. Chem. Res. 1987,20, 207-214. (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 685-702.
34. Earl, R. A.; Townsend, L. B. In Organic Synthesis; Freeman, J. P., Ed.; John Wiley and Sons: New York, 1990; Collect. Vol. VII, pp 334-338.
35. The yield of the cycloadducts depends on the bulkiness of the silyl group. For example, the reaction of 1-(trimethylsiloxy)cyclohexene afforded the desired product in only 12% yield.
36. The stereochemistry of 5, 6, 9, and 11 was established by X-ray crystallographic structure determination of the corresponding derivatives (Supporting Information). The stereochemistry of 8 and 10 was suggested from the analogy to that of 9 and 11.
37. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57-575.
38. Seyferth, D.; Nestle, M. O.; Wehman, A. T. J. Am. Chem. Soc. 1975, 97, 7417-7426.
39. A similar transformation of an acyclic acetylene dicobalt hexacarbonyl complex was reported: Schottelius, M. J.; Chen, P. Helv. Chim. Acta 1998, 81, 2341-2347.