Intermolecular cycloaddition of N-boranonitrone with alkenes

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7164-7174

  Morita, Nobuyoshi ^a   Fukui, Kenji ^a   Irikuchi, Jinshi ^a   Sato, Hiroshi ^a   Takano, Yuu ^a   Okamoto, Iwao ^a   Ishibashi, Hiroyuki ^b   Tamura, Osamu ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS; OLEFINS;

CHEMICAL EQUATIONS; ETHYL GLYOXYLATE; INTERMOLECULAR CYCLOADDITION;

CHEMICAL REACTIONS;

1 METHYLCYCLOHEXENE; 1 METHYLCYCLOPENTENE; 6A METHYLOCTAHYDROCYCLOPENTA[C]PYRROLE 1 CARBOXYLIC ACID ETHYL ESTER; 7A METHYLOCTAHYDROBENZO[D]ISOXAZOLE 3 CARBOXYLIC ACID ETHYL ESTER; ALKENE DERIVATIVE; BORANE DERIVATIVE; ETHYL GLYOXYLATE O TERT BUTYL DIMETHYLSILYL OXIME; GLYOXYLIC ACID DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; N BORANONITRONE; NITROGEN DERIVATIVE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; ISOMER; SYNTHESIS;

ALKENES; AMINO ALCOHOLS; BORANES; CYCLIZATION; ISOXAZOLES; MOLECULAR STRUCTURE; NITROGEN OXIDES; STEREOISOMERISM;

EID: 52449095251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800878p     Document Type: Article

References (58)

1. For reviews, see: (a) Lombardo, M.; Trombini, C. Synthesis 2000, 759.
2. (b) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442.
3. (c) Bloch, R. Chem. Rev. 1998, 98, 1407.
4. (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
5. For leading references, see: (e) Chevrier, C.; Nouen, D. L.; Defoin, A.; Tarnus, C. Eur. J. Org. Chem. 2006, 2384.
6. (f) Merino, P.; Mannucci, V.; Tejero, T. Tetrahedron 2005, 61, 3335.
7. (g) Okino, T.; Hoashi, Y.; Takemoto, Y. Tetrahedron Lett. 2003, 44, 2817.
8. (h) Merino, P.; Tejero, T. Tetrahedron 2001, 57, 8125.
9. (i) Merino, P.; Franco, S.; Gascon, J. M.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1999, 10, 1867.
10. (a) Villamena, F. A.; Merle, J. K.; Hadad, C. M.; Zweier, J. L. J. Phys. Chem. A 2007, 111, 9995.
11. (b) Ueda, M.; Miyabe, H.; Teramachi, M.; Miyata, O.; Naito, T. J. Org. Chem. 2005, 70, 6653.
12. (c) Ueda, M.; Miyabe, H.; Teramachi, M.; Miyata, O.; Naito, T. Chem. Commun. 2003, 426.
13. For reviews, see: (a) Runa, P.; Subhash, G.; Koushik, C.; Amit, B. Synlett 2007, 2321.
14. (b) Cardona, F.; Goti, A., Angew. Chem., Int. Ed. 2005, 44, 7832.
15. (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449.
16. (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
17. (e) Ukaji, Y.; Inomata, K. Synlett 2003, 1075.
18. (f) Kanemasa, S. Synlett 2002, 1371.
19. (g) Pedro, D. M.; Marta, F.; Josep, F. Heterocycles 1999, 50, 1213.
20. (h) Frederickson, M. Tetrahedron 1997, 53, 403.
21. For leading references, see: (i) Partidge, K. M.; Anzovino, M. E.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 2920.
22. (j) Shirahase, M.; Kanemasa, S.; Hasegawa, M. Tetrahedron Lett. 2004, 45, 4061.
23. (k) White, J. D.; Hansen, J. D. J. Am. Chem. Soc. 2002, 124, 4950.
24. (l) Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633.
25. For pioneering works, see: (a) Wildman, W. C.; Slabaugh, M. R. J. Org. Chem. 1971, 36, 3202.
26. (b) Oppolzer, W.; Keller, K. Tetrahedron Lett. 1970, 11, 1117.
27. For recent examples, see: (a) Singh, S.; Ishar, M. P. S.; Singh, G.; Singh, R. Can. J. Chem. 2005, 83, 260.
28. (b) Noguchi, M.; Okada, H.; Tanaka, M.; Matsumoto, S.; Kakehi, A.; Yamamoto, H. Bull. Chem. Soc. Jpn. 2001, 74, 917.
29. (c) Cheng, Q.; Zhang, W.; Tagami, Y.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 2001, 452.
30. (d) Falb, E.; Bechor, Y.; Nudelman, A.; Hassner, A.; Albeck, A.; Gottlieb, H. E. J. Org. Chem. 1999, 64, 498.
31. (e) Dransfield, P. J.; Moutel, S.; Shipman, M.; Sik, V. J. Chem. Soc., Perkin Trans. 1 1999, 3349.
32. (f) Sharma, G. V. M.; Srinivas Reddy, I.; Goverdhan Reddy, V.; Rama Rao, A. V. Tetrahedron: Asymmetry 1999, 10, 229.
33. (g) Baskaran, S.; Aurich, H. G. Synlett 1998, 277.
34. (h) Abiko, A.; Liu, J.-F.; Wang, G.; Masamune, S. Tetrahedron Lett. 1997, 38, 3261.
35. (i) Hassner, A.; Maurya, R.; Friedman, A.; Gottlib, H. E.; Padwa, A.; Austin, D. J. Org. Chem. 1993, 58, 4539.
36. (j) Hassner, A.; Singh, S.; Sharma, R.; Maurya, R. Tetrahedron 1993, 49, 2317.
37. (k) Hassner, A.; Maurya, R.; Padwa, A.; Bullock, W. H. J. Org. Chem. 1991, 56, 2775.
38. 2] by theoretical analysis. See: Long, J. A.; Harris, N. J.; Lammertsma, K. J. Org. Chem. 2001, 66, 6762.
39. (a) Shirai, M.; Kuwabara, H.; Matsumoto, S.; Yamamoto, H.; Kakehi, A.; Noguchi, M. Tetrahedron 2003, 59, 4113.
40. (b) Grigg, R.; Thianpantagul, S. J. Chem. Soc., Perkin Trans. 1 1984, 653.
41. Frederickson, M.; Grigg, R.; Thomton-Pett, M.; Redpath, J. Tetrahedron Lett. 1997, 38, 7777.
42. (a) Tamura, O.; Mitsuya, T.; Huang, X.; Tsutsumi, Y.; Hattori, S.; Ishibashi, H. J. Org. Chem. 2005, 70, 10720.
43. (b) Tamura, O.; Mitsuya, T.; Ishibashi, H. Chem. Commun. 2002, 1128.
44. (a) Grecian, S.; Desai, P.; Mossman, C.; Poutsma, J. L.; Aube, J. J. Org. Chem. 2007, 72, 9439.
45. (b) Ma, Y.; Lobkovsky, E.; Collum, D. B. J. Org. Chem. 2005, 70, 2335.
46. (c) Gossauer, A.; Fehr, F.; Nydegger, F.; Stockli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599.
47. (d) Shoemaker, J. A. W.; Hartman, J. S. Can. J. Chem. 1999, 77, 1856.
48. (e) Hartman, J. S.; Yuan, Z.; Fox, A.; Nguyen, A. Can. J. Chem. 1996, 74, 2131.
49. Tamura, O.; Morita, N.; Takano, Y.; Fukui, K.; Okamoto, I.; Haung, X.; Tsutsumi, Y.; Ishibashi, H. Synlett 2007, 658. Quite recently, N-nonsubstituted isoxazolidines were also obtained by cycloaddition of N-nosyl nitrones with alkenes followed by deprotection with a thiol. See ref 3i.
50. Hoffmann, R. V.; Buntain, G. A. Synthesis 1987, 831.
51. 2 are essential. See ref 9.
52. Adachi, I.; Yamamori, T.; Hiramatsu, Y. JP 1977-50939.
53. (a) Tamura, O.; Shiro, T.; Ogasawara, M.; Toyao, A.; Ishibashi, H. J. Org. Chem. 2005, 70, 4569.
54. (b) Baldwin, S. W.; Long, A. Org. Lett. 2004, 6, 1653.
55. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725.
56. (a) Stauffer, C. S.; Bhaket, P.; Fothergill, A. W.; Rinaldi, M. G.; Datta, A. J. Org. Chem. 2007, 72, 9991.
57. (b) Iida, H.; Kasahara, K.; Kibayashi, C. J. Am. Chem. Soc. 1986, 108, 4647.
58. (c) Tufariello, J. J. Acc. Chem. Res. 1979, 32, 396.