Lewis acid-mediated rearrangement of activated cyclic amines: A facile synthetic protocol for the preparation of amino carbonyl compounds

Journal of Organic Chemistry

Volumn 72, Issue 26, 2007, Pages 10141-10146

  Selvakumar, Sermadurai ^a   Baktharaman, Sivaraj ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO CARBONYL COMPOUNDS; CYCLIC AMINES; LEWIS ACIDS;

AMINES; METHANOL; REACTION KINETICS;

AROMATIC COMPOUNDS;

AMINE; AZETIDINEMETHANOL; CARBONYL DERIVATIVE; LEWIS ACID; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

AMINES; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 37549004052     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702044k     Document Type: Article

References (53)

1. (a) Seebach, D.; Matthews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015-2022.
2. (b) Juaristi, E. In Enantioselective Synthesis of β-amino acids; John Wiley & Sons: New York, 1997.
3. (a) Davis, F. A.; Santhanaraman, M. J. Org. Chem. 2006, 71, 4222-4226.
4. (b) Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011-5014.
5. (c) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F. J. Org. Chem. 2003, 68, 9624-9634.
6. (a) Dimmock, J. R.; Sidhu, K. K.; Chen, M.; Reid, R. S.; Allen, T. M.; Kao, G. Y.; Truitt, G. A. Eur. J. Med. Chem. 1993, 28, 313-322.
7. (b) Traxler, P.; Trinks, U.; Buchdunger, E.; Mett, H.; Meyer, T.; Müller, M.; Regenass, U.; Rösel, N.; Lydon, N. J. Med. Chem. 1995, 38, 2441-2448.
8. (a) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15.
9. (b) Cheng, R. P.; Gellman, S. H.; Degrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
10. (c) Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290-4299.
11. (d) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
12. (e) Mario, O.; Carlos, C. Tetrahedron: Asymmetry 2007, 18, 3-99.
13. (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070.
14. (b) Córdova, A. Acc. Chem. Res. 2004, 37, 102-112.
15. (c) Aziz, N.; Torkiyan, L.; Saidi, M. R. Org. Lett. 2006, 10, 2079-2082.
16. (d) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791-1837.
17. (e) Xu, L.-W.; Xia, C.-G. Eur. J. Org. Chem. 2005, 633-639.
18. (f) Spencer, J. B.; Gaunt, M. J. Org. Lett. 2001, 3, 25-28.
19. (g) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. 1995, 34, 455-457.
20. (h) Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
21. (i) Myers, J. K.; Jacobson, E. N. J. Am. Chem. Soc. 1999, 127, 8959-8960.
22. (j) Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958-1960.
23. (k) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180-8186 and references cited therein.
24. (a) Wang, B. M.; Song, Z. L.; Fan, C. A.; Tu, Y. Q.; Shi, Y. Org. Lett. 2002, 4, 363-366.
25. (b) Song, Z. L.; Wang, B. M.; Tu, Y. Q.; Fan, C. A.; Zhang, S. Y. Org. Lett. 2003, 5, 2319-2321.
26. (c) Molander, G. A.; Stengel, P. J. Tetrahedron 1997, 53, 8887-8912.
27. (d) For a related example of rearrangement of epoxy alcohol for the preparation of β-hydroxy carbonyl compounds, see: Shimazaki, M.; Hara, H.; Suzuki, K.; Tsuchihashi, G.-I. Tetrahedron Lett. 1987, 28, 5891-5894.
28. (a) Prasad, B. A. B.; Bisai, A.; Singh, V. K. Org. Lett. 2004, 6, 4829-4831.
29. (b) Gandhi, S.; Bisai, A.; Prasad, B. A. B.; Singh, V. K. J. Org. Chem. 2007, 72, 2133-2142.
30. Baktharaman, S.; Selvakumar, S.; Singh, V. K. Org. Lett. 2006, 8, 4335-4338.
31. Yang, S.-D.; Shi, Y.; Sun, Z.-H.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 1895-1900.
32. Bhaskar Kanth, J. V.; Periasamy, M. Tetrahedron 1993, 49, 5127-5132.
33. Under the specified condition, the reaction failed to give any ring-opening product when diphenyl is replaced by dialkyl or monophenyl.
34. Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212-8216.
35. Nishizawa, M.; Asai, Y.; Imagawa, H. Org. Lett. 2006, 8, 5793-5796.
36. (a) Ibuka, T.; Nakai, K.; Akaji, M.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron 1996, 52, 11739-11752.
37. (b) Nakai, K.; Ibuka, T.; Otaka, A.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 6247-6250.
38. (c) Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett. 1992, 33, 5351-5354.
39. (d) Bouyacoub, A.; Volatron, F. Eur. J. Org. Chem. 2002, 24, 4143-4150.
40. (e) Moulines, J.; Charpentier, P.; Bats, J.-P.; Nuhrich, A.; Lamidey, A.-M. Tetrahedron Lett. 1992, 33, 487-490.
41. (f) Atkinson, R. S.; Fawcett, J.; Russell, D. R.; Williams, P. J. Tetrahedron Lett. 1995, 36, 3241-3244.
42. (g) Ibuka, T.; Nakai, K.; Habashita, H.; Fujii, N.; Garrido, F.; Mann, A. Tetrahedron Lett. 1993, 34, 7421-7424.
43. (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fuji, N.; Mimura, N.; Miwa, Y.; Taga, T.; Chounan, Y.; Yamamoto, Y. J. Org. Chem. 1995, 60, 2044-2058.
44. (b) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145-154.
45. (c) Schomaker, J. M.; Bhattacharjee, S.; Yan, J.; Borhan, B. J. Am. Chem. Soc. 2007, 129, 1996-2003.
46. (d) Rosser, C. M.; Coote, S. C.; Kirby, J. P.; O'Brien, P.; Caine, D. Org, Lett. 2004, 6, 4817-4819.
47. (e) Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726-8743 and references cited therein.
48. Xichun, F.; Guofu, Q.; Shucai, L.; Hanbing, T.; Lamei, W.; Xianming, H. Tetrahedron: Asymmetry 2006, 17, 1394-1401.
49. The exposure of 1a to base NaH in THF/HMPA (10:1) did not affect it even after 24 h.
50. R = 42.97 min.
51. (b) The reaction of epoxide derived from aza-Payne rearrangement of 13, with Lewis acid under standard condition afforded the hydride migrated product in 16% yield (Based on recovered starting material) after 14 h.
52. Rama Rao, A. V.; Gurjar, M. K.; Sharma, P. A.; Kumar, V. Tetrahedron Lett. 1990, 31, 2341-2344.
53. Wasserman, H. H.; Lipshutz, B. H.; Tremper, A. W.; Wu, J. S. J. Org. Chem. 1981, 46, 2991-2999.