Intramolecular [3 + 2] annulation of olefin-tethered cyclopropylamines

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8510-8514

  Ha, Jae Du ^a   Lee, Jinhwa ^a   Blackstock, Silas C ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE OXIDASE (FLAVIN CONTAINING); CYTOCHROME P450; PROPYLAMINE;

ARTICLE; DIASTEREOISOMER; ENZYME ACTIVITY; OXIDATION; PHOTOCHEMISTRY; PHOTOOXIDATION; PHOTOSENSITIZATION;

EID: 0000179171     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9817671     Document Type: Article

References (44)

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4. This new synthetic method for electron-donor substituted cyclopropanes, in turn, evolved from the original Kulinkovich procedure: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294. (c) Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
5. This new synthetic method for electron-donor substituted cyclopropanes, in turn, evolved from the original Kulinkovich procedure: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294. (c) Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
6. (a) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996,118, 291.
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11. See also: (e) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (f) Lee, J.; Cha, J. K. Tetrahedron Lett. 1996, 37, 3663. (g) U, J. S.; Lee, J.; Cha, J. K. Tetrahedron Lett. 1997, 38, 5233. (h) Lee, J.; Ha, J. D.; Cha, J. K J. Am. Chem. Soc. 1997, 119, 8127.
12. See also: (e) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (f) Lee, J.; Cha, J. K. Tetrahedron Lett. 1996, 37, 3663. (g) U, J. S.; Lee, J.; Cha, J. K. Tetrahedron Lett. 1997, 38, 5233. (h) Lee, J.; Ha, J. D.; Cha, J. K J. Am. Chem. Soc. 1997, 119, 8127.
13. See also: (e) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (f) Lee, J.; Cha, J. K. Tetrahedron Lett. 1996, 37, 3663. (g) U, J. S.; Lee, J.; Cha, J. K. Tetrahedron Lett. 1997, 38, 5233. (h) Lee, J.; Ha, J. D.; Cha, J. K J. Am. Chem. Soc. 1997, 119, 8127.
14. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references therein.
15. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references therein.
16. See also: (a) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079. (c) Kasatkin, A.; Kobayashi, K; Okamoto, S.; Sato, F. Tetrahedron Lett. 1996, 37, 1849 and references therein.
17. Kuehne, M. E.; King, J. C. J. Org. Chem. 1973, 38, 304.
18. Lee, J.; U, J. S.; Blackstock, S. C.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 10241.
19. See, inter alia: (a) Guengerich, F. P.; Macdonald, T. L. Adv. Electron Transfer Chem. 1993, 3, 191. (b) Hanzlik, R. P.; Tullman, R. H. J. Am. Chem. Soc. 1982, 104, 2048. (c) Silverman, R. B. J. Biol. Chem. 1983, 258, 14766. See also: (d) Pirrung, M. C. J. Am. Chem. Soc. 1983, 105, 7207.
20. See, inter alia: (a) Guengerich, F. P.; Macdonald, T. L. Adv. Electron Transfer Chem. 1993, 3, 191. (b) Hanzlik, R. P.; Tullman, R. H. J. Am. Chem. Soc. 1982, 104, 2048. (c) Silverman, R. B. J. Biol. Chem. 1983, 258, 14766. See also: (d) Pirrung, M. C. J. Am. Chem. Soc. 1983, 105, 7207.
21. See, inter alia: (a) Guengerich, F. P.; Macdonald, T. L. Adv. Electron Transfer Chem. 1993, 3, 191. (b) Hanzlik, R. P.; Tullman, R. H. J. Am. Chem. Soc. 1982, 104, 2048. (c) Silverman, R. B. J. Biol. Chem. 1983, 258, 14766. See also: (d) Pirrung, M. C. J. Am. Chem. Soc. 1983, 105, 7207.
22. See, inter alia: (a) Guengerich, F. P.; Macdonald, T. L. Adv. Electron Transfer Chem. 1993, 3, 191. (b) Hanzlik, R. P.; Tullman, R. H. J. Am. Chem. Soc. 1982, 104, 2048. (c) Silverman, R. B. J. Biol. Chem. 1983, 258, 14766. See also: (d) Pirrung, M. C. J. Am. Chem. Soc. 1983, 105, 7207.
23. For recent investigations on kinetics of other aminium radical reactions, see: (a) Goez, M.; Satorius, I. J. Am. Chem. Soc. 1993, 115, 11123. (b) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124. (c) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862. Cf.: (d) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
24. For recent investigations on kinetics of other aminium radical reactions, see: (a) Goez, M.; Satorius, I. J. Am. Chem. Soc. 1993, 115, 11123. (b) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124. (c) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862. Cf.: (d) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
25. For recent investigations on kinetics of other aminium radical reactions, see: (a) Goez, M.; Satorius, I. J. Am. Chem. Soc. 1993, 115, 11123. (b) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124. (c) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862. Cf.: (d) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
26. For recent investigations on kinetics of other aminium radical reactions, see: (a) Goez, M.; Satorius, I. J. Am. Chem. Soc. 1993, 115, 11123. (b) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124. (c) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862. Cf.: (d) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
27. For recent examples of intramolecular hydrogen atom transfer, see inter alia: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in the Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, p 161. (b) Baldwin, J. E.; Adlington, R. M.; Robertson, J. Tetrahedron 1989, 45, 909. (c) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (d) White, J. D.; Jeffrey, S. C. Synlett 1995, 831.
28. For recent examples of intramolecular hydrogen atom transfer, see inter alia: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in the Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, p 161. (b) Baldwin, J. E.; Adlington, R. M.; Robertson, J. Tetrahedron 1989, 45, 909. (c) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (d) White, J. D.; Jeffrey, S. C. Synlett 1995, 831.
29. For recent examples of intramolecular hydrogen atom transfer, see inter alia: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in the Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, p 161. (b) Baldwin, J. E.; Adlington, R. M.; Robertson, J. Tetrahedron 1989, 45, 909. (c) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (d) White, J. D.; Jeffrey, S. C. Synlett 1995, 831.
30. For recent examples of intramolecular hydrogen atom transfer, see inter alia: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in the Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, p 161. (b) Baldwin, J. E.; Adlington, R. M.; Robertson, J. Tetrahedron 1989, 45, 909. (c) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896. (d) White, J. D.; Jeffrey, S. C. Synlett 1995, 831.
31. In a previous communication (footnote 17 of ref 7), we had disclosed that the ring-opened, β-immonium carbon radical can be trapped effectively by a tethered olefin by means of 5-exo cyclization, affording efficient bicyclic annulation.
32. A recent report on the related CAN-mediated cyclization prompted us to report our own results: Takemoto, Y.; Yamagata, S.; Furuse, S.-i.; Hayase, H.; Echigo, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1998, 651.
33. Cyclopropyl sulfides bearing a benzylidene moiety were shown to undergo similiar cyclization: Takemoto, Y.; Furuse, S.-i.; Koike, H.; Ohra, T.; Iwata, C.; Ohishi, H. Tetrahedron Lett. 1995, 36, 4085.
34. Whereas the stereochemistry has not been assigned yet, it is likely that 16 has the piperidine ring in the β configuration (with the a configuration of the cyclopentyl group).
35. + = 9.2): Roberts, J. D.; Chambers, V. C. J. Am. Chem. Soc. 1951, 73, 5030.
36. (a) This solvent system was originally and successfully employed for the generation of the ring-opened ketones by photosensitized oxidation of tertiary aminocyclopropanes (ref 7). (b) While the reason for the beneficial effect of water is presently unclear, it is tempting to speculate that it might be in part due to H-bonding between water and the tertiary amine.
37. Cf.: (a) Nelsen, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, Chapter 21. (b) Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (d) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163. (e) Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211 and references therein.
38. Cf.: (a) Nelsen, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, Chapter 21. (b) Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (d) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163. (e) Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211 and references therein.
39. Cf.: (a) Nelsen, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, Chapter 21. (b) Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (d) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163. (e) Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211 and references therein.
40. Cf.: (a) Nelsen, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, Chapter 21. (b) Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (d) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163. (e) Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211 and references therein.
41. Cf.: (a) Nelsen, S. F. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, Chapter 21. (b) Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (d) Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc. 1987, 109, 3163. (e) Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211 and references therein.
42. The formamide formation is presumed to arise from oxidation of the enamine intermediate 29. The detailed mechanism must await further study. Cf.: (a) Jerussi, R. A. J. Org. Chem. 1969, 34, 3648. (b) Blau, K.; Voerckel, V. J. Prakt. Chem. 1989, 331, 285.
43. The formamide formation is presumed to arise from oxidation of the enamine intermediate 29. The detailed mechanism must await further study. Cf.: (a) Jerussi, R. A. J. Org. Chem. 1969, 34, 3648. (b) Blau, K.; Voerckel, V. J. Prakt. Chem. 1989, 331, 285.
44. 12 On the basis of our present findings, we believe their proposed timing of debenzylation is incorrect; the correct debenzylation mechanism involves the identical sequence as described for 8a → 27 → 28 → 25.