The Rearrangement Route to 3-CH2X-2-azabicyclo[2.1.1 ]hexanes. Substituent Control of Neighboring Group Participation

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1259-1262

  Krow, Grant R ^a   Yuan, Jing ^a   Lin, Guoliang ^a   Sonnet, Philip E ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0013374665     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020007g     Document Type: Article

References (35)

1. (a) Piela, L.; Nemethy, G.; Scheraga, H. A. J. Am. Chem. Soc. 1987, 109, 4477.
2. (b) Montelione, G. T.; Hughes, P.; Clardy, J.; Scheraga, H. A. J. Am. Chem. Soc. 1986, 108, 6765.
3. (c) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875.
4. Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
5. Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
6. (a) Lynch, J. K.; Holladay, M. W.; Ryther, K. B.; Bai, H.; Hsiao, C.-N.; Morton, H. E.; Dickman, D. A.; Arnold, W.; King, S. A. Tetrahedron: Asymmetry 1998, 9, 2791.
7. (b) Bannon, A. W.; Decker, M. W.; Holladay, M. W.; Curzon, P.; Donnelly-Roberts, D.; Puttfarcken, P. S.; Bitner, R. S.; Diaz, A.; Dickerson, A. H.; Porsolt, R. D.; Williams, M.; Arneric, S. P. Science 1998, 279, 77.
8. For a library based upon 4-hydroxyproline, see: Goldberg, M.; Smith, L., II; Tamayo, N.; Kiselyov, A. S. Tetrahedron 1999, 55, 13887. For a library based upon amide diols, see; Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735.
9. For a library based upon 4-hydroxyproline, see: Goldberg, M.; Smith, L., II; Tamayo, N.; Kiselyov, A. S. Tetrahedron 1999, 55, 13887. For a library based upon amide diols, see; Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735.
10. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
11. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
12. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
13. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
14. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
15. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
16. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
17. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
18. For photochemical routes, see: (a) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1979, 44, 1380. (b) Pirrung, M. C. Tetrahedron Lett. 1980, 21, 4577. (c) Hughes, P.; Martin, M.; Clardy, J. Tetrahedron Lett. 1980, 21, 4579. (d) Hughes, P.; Clardy, J. J. Org. Chem. 1988, 53, 4793. (e) Tamura, Y.; Ishibashi, H.; Hirai, M.; Kita, Y.; Ikeda, M. J. Org. Chem. 1975, 40, 2702. (f) Ikeda, M.; Uchno, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Swindel, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. (h) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlain, A. R.; Thompson, C. M.; Bridges. Bioorg. Med. Chem. Lett. 1998, 8, 3101. (i) Piotrowski, D. W. Synlett. 1999, 1091.
19. For nucleophilic substitution ring closure routes, see ref 2 and (a) Gaoni, Y. Org. Prep. Proced. Int. 1995, 27, 185. (b) Stevens, C.; De Kimpe, N. J. Org. Chem. 1996, 61, 2174. (c) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187.
20. For nucleophilic substitution ring closure routes, see ref 2 and (a) Gaoni, Y. Org. Prep. Proced. Int. 1995, 27, 185. (b) Stevens, C.; De Kimpe, N. J. Org. Chem. 1996, 61, 2174. (c) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187.
21. For nucleophilic substitution ring closure routes, see ref 2 and (a) Gaoni, Y. Org. Prep. Proced. Int. 1995, 27, 185. (b) Stevens, C.; De Kimpe, N. J. Org. Chem. 1996, 61, 2174. (c) Lescop, C.; Mevellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187.
22. (a) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Christian, H.; Shaw, D. A.; Yuan, J. J. Org. Chem. 1998, 63, 8558.
23. (b) Krow, G. R.; Lester, W. S.; Liu, N.; Yuan, J.; Hiller, A.; Duo, J.; Herzon, S. B.; Nguyen, Y.; Cannon, K. J. Org. Chem. 2001, 66, 1811.
24. (c) Krow, G. R.; Lee, Y. B.; Lester, W. S.; Liu, N.; Yuan, J.; Duo, J.: Herzon, S. B.; Nguyen, Y.; Zacharias, D. J. Org. Chem. 2001, 66, 1805.
25. Krow, G. R.; Yuan, J.; Fang, Y.; Meyer, M. D.; Anderson, D. J.; Campbell, J. E.; Carroll, P. J. Tetrahedron 2000, 56, 9227.
26. Dalton, D. R.; Rodebaugh, R. K.; Jefford, J. Org. Chem. 1972, 37, 362.
27. Neighboring group participation by the double-bonded oxygen of a tosylate has been postulated. Boyle, P. H.; Coy, J. H. J. Org. Chem. 1973, 38, 826.
28. Sulfur-oxygen cleavage under nucleophilic solvolytic conditions is known. (a) Gassman, P. G.; Hornback, J. M.; Pascone, J. M. Tetrahedron Lett. 1971, 12, 1425. (b) Xu, C.-L.; Chen, Z.-C, Tetrahedron Lett. 1991, 32, 2933. (c) Precedent for sulfur-oxygen bond cleavage of tosylates in other than strongly nucleophilic solvolytic conditions is sparse. See ref 10. In the solvolysis of fluorinated alkyl tosylates, which contain electron-poor alkyl groups, no measurable cleavage of the alkyl-oxygen bond occurred in 98% sulfuric acid. Drabicky, M. J.; Myhre, P. C.; Reich, C. J.; Schmittour, E. R. J. Org. Chem. 1976, 41, 1472.
29. Sulfur-oxygen cleavage under nucleophilic solvolytic conditions is known. (a) Gassman, P. G.; Hornback, J. M.; Pascone, J. M. Tetrahedron Lett. 1971, 12, 1425. (b) Xu, C.-L.; Chen, Z.-C, Tetrahedron Lett. 1991, 32, 2933. (c) Precedent for sulfur-oxygen bond cleavage of tosylates in other than strongly nucleophilic solvolytic conditions is sparse. See ref 10. In the solvolysis of fluorinated alkyl tosylates, which contain electron-poor alkyl groups, no measurable cleavage of the alkyl-oxygen bond occurred in 98% sulfuric acid. Drabicky, M. J.; Myhre, P. C.; Reich, C. J.; Schmittour, E. R. J. Org. Chem. 1976, 41, 1472.
30. Sulfur-oxygen cleavage under nucleophilic solvolytic conditions is known. (a) Gassman, P. G.; Hornback, J. M.; Pascone, J. M. Tetrahedron Lett. 1971, 12, 1425. (b) Xu, C.-L.; Chen, Z.-C, Tetrahedron Lett. 1991, 32, 2933. (c) Precedent for sulfur-oxygen bond cleavage of tosylates in other than strongly nucleophilic solvolytic conditions is sparse. See ref 10. In the solvolysis of fluorinated alkyl tosylates, which contain electron-poor alkyl groups, no measurable cleavage of the alkyl-oxygen bond occurred in 98% sulfuric acid. Drabicky, M. J.; Myhre, P. C.; Reich, C. J.; Schmittour, E. R. J. Org. Chem. 1976, 41, 1472.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
32. Intermediate 9 might be expected to ring open by attack of water at (Matrix Presented)
33. For synthesis of a 4-aminomethyl-2-azabicyclo[2.1.1]hexane, see ref 2. For synthesis of a 5-aminomethyl-2-azabicyclo[2.1.1]hexane, see ref 6c.
34. Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869.
35. Sakaitani, M.; Hori, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 2983.