A new strategy for construction of eight-membered carbocycles by Brook rearrangement mediated [6 + 2] annulation

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3705-3707

  Takeda, Kei ^a,b   Haraguchi, Hidekazu ^a   Okamoto, Yasushi ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142106410     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0353767     Document Type: Article

References (36)

1. (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930.
2. (b) Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
3. (c) Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282.
4. (d) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
5. (a) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401.
6. (b) Takeda, K.; Nakajima, A.; Yoshii, E. Synlett 1996, 753-754.
7. (c) Takeda, K.; Nakane, D.; Takeda, M. Org. Lett. 2000, 2, 1903-1905.
8. (d) Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 4947-4959.
9. (e) Takeda, K.; Nakajima, A.; Takeda, M.; Yoshii, E.; Zhang, J.; Boeckman, R. K., Jr. Org. Synth. 1999, 76, 199-213.
10. (f) Takeda, K.; Ohtani, Y. Org. Lett. 1999, 1, 677-679.
11. Takeda, K.; Sawada, Y.; Sumi K. Org. Lett. 2002, 4, 1031-1033.
12. (a) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020.
13. (b) Wilson, S. R. Org. React. 1993, 43, 93-250.
14. (c) Bronson, J. J.; Danheiser, R. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 999-1036.
15. (d) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 785-826.
16. (e) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626.
17. Also, see: (f) Gadwood, R. C.; Lett, R. M. J. Org. Chem. 1982, 47, 2268-2275.
18. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
19. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
20. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
21. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
22. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
23. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
24. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
25. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84. For the use of the Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F. ; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
26. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
27. Scheller, M. E.; Frei, B. Helv. Chim. Acta 1984, 67, 1734-1747.
28. For intramolecular chelation involving pentacoordinate silicon species: (a) see ref 2d. (b) Takeda, K.; Yamawaki, K.; Hatakeyama, N. J. Org. Chem. 2002, 67, 1786-1794. (c) Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
29. For intramolecular chelation involving pentacoordinate silicon species: (a) see ref 2d. (b) Takeda, K.; Yamawaki, K.; Hatakeyama, N. J. Org. Chem. 2002, 67, 1786-1794. (c) Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
30. For intramolecular chelation involving pentacoordinate silicon species: (a) see ref 2d. (b) Takeda, K.; Yamawaki, K.; Hatakeyama, N. J. Org. Chem. 2002, 67, 1786-1794. (c) Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
31. In the reactions of 11b-d, 12b-d were the only identifiable products.
32. Takeda, K.; Tanaka, T. Synlett 1999, 705-708.
33. Jacobson, R. M.; Lahm, G. P.; Clader, J. W. J. Org. Chem. 1980, 45, 395-405.
34. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
35. For conversion of the γ-silyl enol silyl ethers into enones, see ref 2d.
36. Chich, P. C.; Trotter, J. J. Chem. Soc. A 1969, 1778-1783.