Azomethine ylides from tin-substituted cyclic carbinol amides: A new route to highly substituted pyrrolizidines

Organic Letters

Volumn 6, Issue 6, 2004, Pages 1005-1008

  Pearson, William H ^a,b   Dietz, Amber ^a   Stoy, Patrick ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Berry and Associates Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AZOMETHINE YLIDE; MAGNESIUM DERIVATIVE; METHANOL DERIVATIVE; N (TRIBUTYLSTANNYLMETHYL)CYCLIC CARBINOL AMIDE DERIVATIVE; N (TRIBUTYLSTANNYLMETHYL)PHTHALIMIDE DERIVATIVE; ORGANOLITHIUM COMPOUND; PHTHALIMIDE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; REAGENT; TIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SUBSTITUTION REACTION; SYNTHESIS;

AMIDES; HETEROCYCLIC COMPOUNDS; LITHIUM; METHANOL; PHTHALIMIDES; PYRROLIZIDINE ALKALOIDS; TIN;

EID: 1642446230     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0499304     Document Type: Article

References (48)

1. Chong, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220-2222.
2. (a) Pearson, W. H.; Stoy, P. Synlett 2003, 903-921.
3. (b) Pearson, W. H.; Aponick, A. Org. Lett. 2001, 3, 1327-1330.
4. (c) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1992, 57, 6354-6356.
5. Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329-1345.
6. (a) Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1999, 40, 4467-4471.
7. (b) Clark, R. B.; Pearson, W. H. Org. Lett. 1999, 1, 349-351.
8. (c) Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
9. (d) Pearson, W. H.; Stoy, P.; Mi, Y. J. Org. Chem. 2004, in press.
10. (a) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622-2636.
11. (b) Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546-8548.
12. (c) Pearson, W. H.; Lindbeck, A. C. J. Org. Chem. 1989, 54, 5651-5654.
13. Some recent selected examples: (a) Christoph, G.; Hoppe, D. Org. Lett. 2002, 4, 2189-2192. (b) Clayden, J.; Helliwell, M.; Pink, J. H.; Westlund, N. J. Am. Chem. Soc. 2001, 123, 12449-12457. (c) Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196-6201.
14. Some recent selected examples: (a) Christoph, G.; Hoppe, D. Org. Lett. 2002, 4, 2189-2192. (b) Clayden, J.; Helliwell, M.; Pink, J. H.; Westlund, N. J. Am. Chem. Soc. 2001, 123, 12449-12457. (c) Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196-6201.
15. Some recent selected examples: (a) Christoph, G.; Hoppe, D. Org. Lett. 2002, 4, 2189-2192. (b) Clayden, J.; Helliwell, M.; Pink, J. H.; Westlund, N. J. Am. Chem. Soc. 2001, 123, 12449-12457. (c) Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196-6201.
16. N-Acyliminiums derived from cyclic carbinol amides have proved to be useful intermediates in the synthesis of nitrogen-containing heterocycles. See: Rashatasakhon, P.; Padwa, A. Org. Lett. 2003, 5, 189-191 and references therein.
17. (a) Harwood, L. M.; Vickers, R. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002; pp 169-252.
18. (b) Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981-1008.
19. (c) Vedejs, E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich; CT, 1988; Vol. 1, pp 33-51.
20. (d) Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941-955.
21. (a) Padwa, A.; Dent, W. J. Org. Chem. 1987, 52, 235-244.
22. (b) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896-898 and 2762-2766.
23. (c) Hosomi, A.; Sakata, Y.; Sakurai, H. Chem. Lett. 1984, 1117-1120.
24. See ref 8b and: Achiwa, K.; Sekiya, M. Chem. Lett. 1981, 1213-1216.
25. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
26. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
27. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
28. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
29. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
30. For recent synthetic work, see: (a) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525-7539. (b) Reyes, A.; Regla, I.; Fragoso, M. C.; Vallejo, L. A.; Demare, P.; Jimenez-Vazquez, H. A.; Ramirez, Y.; Juaristi, E.; Tamariz, J. Tetrahedron 1999, 55, 11187-11202. (c) Luzzio, F. A.; Zacherl, D. P. Tetrahedron Lett. 1998, 39, 2285-2288. (d) Ha, D.-C.; Yun, C.-S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580. (e) Grigg, R.; Sriharan, V.; Suganthan, S.; Bridge, A. W. Tetrahedron 1995, 51, 295-306. This ring system has also appeared in studies of cyclin-depedent kinase (Cdk4) inhibitors: (f) Honma, T.; Hayashi, K.; Aoyama, T.; Hashimoto, N.; Machida, T.; Furasawa, K.; Iwama, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Iwasawa, Y.; Hayama, T.; Nishimura, S.; Morishima, H. J. Med. Chem. 2001, 44, 4615-4627 and references therein.
31. (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 2001, 34, 523-533.
32. (b) Takahashi, Y.; Miyashi, T.; Yoon, U. C.; Oh, S. W.; Mancheno, M.; Su, Z.; Falvey, D. F.; Mariano, P. S. J. Am. Chem. Soc. 1999, 121, 3926-3932.
33. (c) Yoon, U. C.; Lee, C. W.; Oh, S. W.; Mariano, P. S. Tetrahedron 1999, 55, 11997-12008.
34. (d) Yoon, U. C.; Kim, D. U.; Lee, C. W.; Choi, Y. S.; Lee, Y.-J.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698-2710.
35. (e) Yoon, U. C.; Cho, S. J.; Lee, Y.-J.; Mancheno, M. J.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353-2360.
36. For examples of bridgehead substitution in 1-aza[m.3.0]bicycloalkanes derived from the intermolecular cycloaddition of azomethine ylides, see ref 4c and: (a) Epperson, M. T.; Gin D. Y. Angew. Chem., Int. Ed. 2002, 41, 1778-1780. (b) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486. (c) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1992, 2331-2335.
37. For examples of bridgehead substitution in 1-aza[m.3.0]bicycloalkanes derived from the intermolecular cycloaddition of azomethine ylides, see ref 4c and: (a) Epperson, M. T.; Gin D. Y. Angew. Chem., Int. Ed. 2002, 41, 1778-1780. (b) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486. (c) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1992, 2331-2335.
38. For examples of bridgehead substitution in 1-aza[m.3.0]bicycloalkanes derived from the intermolecular cycloaddition of azomethine ylides, see ref 4c and: (a) Epperson, M. T.; Gin D. Y. Angew. Chem., Int. Ed. 2002, 41, 1778-1780. (b) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486. (c) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1992, 2331-2335.
39. 4Sn.
40. Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1983, 24, 1407-1410.
41. 3 times that of germanium; see: (a) Hagan, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961. (b) Lambert, J. B.; Wang, G-t.; Teramura, D. H. J. Org. Chem. 1988, 53, 5422-5428. (c) Traylor, T. G.; Koermer, G. S. J. Org. Chem. 1981, 46, 3651-3657.
42. 3 times that of germanium; see: (a) Hagan, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961. (b) Lambert, J. B.; Wang, G-t.; Teramura, D. H. J. Org. Chem. 1988, 53, 5422-5428. (c) Traylor, T. G.; Koermer, G. S. J. Org. Chem. 1981, 46, 3651-3657.
43. 3 times that of germanium; see: (a) Hagan, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961. (b) Lambert, J. B.; Wang, G-t.; Teramura, D. H. J. Org. Chem. 1988, 53, 5422-5428. (c) Traylor, T. G.; Koermer, G. S. J. Org. Chem. 1981, 46, 3651-3657.
44. (a) Linderman, R. J.; Chen, K. J. Org. Chem. 1996, 61, 2441-2453.
45. (b) Linderman, R. J.; Anklekar, T. V. J. Org. Chem. 1992, 57, 5078-5080.
46. (a) Cossrow, J.; Rychnovsky, S. D. Org. Lett. 2002, 4, 147-150.
47. (b) Rychnovsky, S. D.; Cossrow, J. Org. Lett. 2003, 5, 2367-2370.
48. (c) Huckins, J. R.; Rychnovsky, S. D. J. Org. Chem. 2003, 68, 10135-10145.