Novel selectfluor and deoxo-fluor-mediated rearrangements. New 5(6)-methyl and phenyl methanopyrrolidine alcohols and fluorides

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1669-1672

  Krow, Grant R ^a   Lin, Guoliang ^a   Moore, Keith P ^a   Thomas, Andrew M ^a   DeBbrosse, Charles ^a   Ross III, Charles W ^b   Ramjit, Harri G ^b  

^a Temple University   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZABICYCLO[2.2.0]HEX 5 ENE EPOXIDE; ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; BICYCLO COMPOUND; COPPER COMPLEX; EPOXIDE; FLUORINE DERIVATIVE; HEXANE; HYDROXYL GROUP; IODINE DERIVATIVE; METHYL GROUP; PYRROLIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; RING OPENING; SYNTHESIS;

EID: 2542546731     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494818     Document Type: Article

References (44)

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12. For reports of 4,6-cyclohexyl-fused methanopyrrolidines, see: (a) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165. (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (c) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1989, 54, 4165. (d) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. For reports of 1,5-cyclohexyl-fused methanopyrrolidines, see: (e) Ikeda, M.; Takahashi, M.; Ohno, K.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1982, 30, 2269. (f) Ikeda, M.; Uchino, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. For a 3,5-cyclopentyl-fused methanopyrrolidine, see: (h) Rammeloo, T.; Stevens, C. V. New. J. Chem. 2003, 27, 668.
13. For reports of 4,6-cyclohexyl-fused methanopyrrolidines, see: (a) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165. (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (c) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1989, 54, 4165. (d) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. For reports of 1,5-cyclohexyl-fused methanopyrrolidines, see: (e) Ikeda, M.; Takahashi, M.; Ohno, K.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1982, 30, 2269. (f) Ikeda, M.; Uchino, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. For a 3,5-cyclopentyl-fused methanopyrrolidine, see: (h) Rammeloo, T.; Stevens, C. V. New. J. Chem. 2003, 27, 668.
14. For reports of 4,6-cyclohexyl-fused methanopyrrolidines, see: (a) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165. (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (c) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1989, 54, 4165. (d) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. For reports of 1,5-cyclohexyl-fused methanopyrrolidines, see: (e) Ikeda, M.; Takahashi, M.; Ohno, K.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1982, 30, 2269. (f) Ikeda, M.; Uchino, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. For a 3,5-cyclopentyl-fused methanopyrrolidine, see: (h) Rammeloo, T.; Stevens, C. V. New. J. Chem. 2003, 27, 668.
15. For reports of 4,6-cyclohexyl-fused methanopyrrolidines, see: (a) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165. (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (c) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1989, 54, 4165. (d) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. For reports of 1,5-cyclohexyl-fused methanopyrrolidines, see: (e) Ikeda, M.; Takahashi, M.; Ohno, K.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1982, 30, 2269. (f) Ikeda, M.; Uchino, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. For a 3,5-cyclopentyl-fused methanopyrrolidine, see: (h) Rammeloo, T.; Stevens, C. V. New. J. Chem. 2003, 27, 668.
16. For reports of 4,6-cyclohexyl-fused methanopyrrolidines, see: (a) Vogler, B.; Bayer, R.; Meller, M.; Kraus, W. J. Org. Chem. 1989, 54, 4165. (b) Kwak, Y.-S.; Winkler, J. D. J. Am. Chem. Soc. 2001, 123, 7429. (c) Schell, F. M.; Cook, P. M.; Hawkinson, S. W.; Cassady, R. E.; Thiessen, W. E. J. Org. Chem. 1989, 54, 4165. (d) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346. For reports of 1,5-cyclohexyl-fused methanopyrrolidines, see: (e) Ikeda, M.; Takahashi, M.; Ohno, K.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1982, 30, 2269. (f) Ikeda, M.; Uchino, T.; Takahashi, M.; Ishibashi, H.; Tamura, Y.; Kido, M. Chem. Pharm. Bull. 1985, 33, 3279. (g) Toda, F.; Miyamoto, H.; Takeda, K.; Matsugawa, R.; Maruyama, N. J. Org. Chem. 1993, 58, 6208. For a 3,5-cyclopentyl-fused methanopyrrolidine, see: (h) Rammeloo, T.; Stevens, C. V. New. J. Chem. 2003, 27, 668.
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