New preparation of activated 2-vinylaziridines from 1,4-aminoalcohols

Synlett

Volumn , Issue 3, 1998, Pages 247-248

  Olivo, Horacio F ^a   Hemenway, Michael S ^a   Hartwig, Amy C ^a   Chan, Raymond ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002577021     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1635     Document Type: Article

References (60)

1. (a) Ibuka, T.; Mimura, N.; Aoyaraa, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N. J. Org. Chem. 1997, 62, 999.
2. (b) Ohno, H.; Mimura, N.; Otaka, A.; Tamamura, H.; Fujii, N.; Ibuka, T.; Shimizu, I.; Satake, A.; Yamamoto, Y. Tetrahedron 1997, 53, 12933.
3. (c) Jähnisch, K. Liebigs Ann. 1997, 757.
4. (d) Åhman, J.; Jarevång, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148.
5. (e) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Chen, M.-B. J. Org. Chem. 1996, 61, 4641.
6. (f) Åhman, J.; Somfai, P. J. Am. Chem. Soc. 1994, 116, 9781.
7. (g) Åhman, J.; Somfai, P.; Tanner, D. J. Chem. Soc., Chem. Commun. 1994, 2785.
8. (h) Tanner, D. Pure & Appl. Chem. 1993, 65, 1319.
9. (i) Spears, G. W.; Nakanishi, K.; Ohfune, Y. Synlett 1991, 91.
10. (j) Hassner, A.; Chau, W. Tetrahedron Lett. 1982, 23, 1989.
11. Hudlicky, T.; Tian, X.; Königsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037.
12. (a) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347.
13. (b) Wipf, P. and Venkatraman, S. Synlett 1997, 1.
14. (c) Åhman, J.; Somfai, P. Tetrahedron Lett. 1996, 37, 2494.
15. (d) Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303.
16. (e) Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. Tetrahedron Lett. 1995, 36, 3557.
17. (f) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje, M.; Seoane, A.; Kwart, L. D.; Beal, C. J. Am. Chem. Soc. 1986, 108, 3755.
18. (g) Hudlicky, T.; Frazier, J. O.; Kwart, L. D. Tetrahedron Lett. 1985, 26, 3523.
19. (h) Pearson, W. H. Tetrahedron Lett. 1985, 26, 3527.
20. (a) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 899.
21. (b) Hudlicky, T.; Seoane, G.; Price, J. D.; Gadamasetti, K. G. Synlett 1990, 433.
22. (c) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. In Studies in Natural Products Chemistry, Atta-Ur-Rahman, Ed.; Elsevier: New York, 1988; Vol. 3, p 3.
23. (a) Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752.
24. (b) Tian, X.; Hudlicky, T.; Königsberger, K. J. Am. Chem. Soc. 1995, 117, 3643.
25. (a) Knight, J. G.; Muldowney, M. P. Synlett 1995, 949.
26. (b) Tanner, D.; Anderson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4631.
27. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
28. (d) Li, A.-H.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1996, 491.
29. Vedejs, E.; Lin, S. J. Org. Chem. 1994, 59, 1602.
30. (a) Wessig, P. and Schwarz, J. Synlett 1997, 893.
31. (b) Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.
32. (c) Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Org. Chem. 1996, 61, 8368.
33. (d) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64.
34. (a) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
35. (b) Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
36. (a) Baldwin, J. E.; Farthing, C. N.; Russell, A. T.; Schofield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761.
37. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722.
38. (c) Osborn, H. M. I.; Cantrill, A. A.; Sweeney, J. B. Tetrahedron Lett. 1994, 35, 3159.
39. (d) Backes, J. In Organic Nitrogen Compounds III; 4th ed.; Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1992; Vol. E16c, p 370.
40. (e) Backes, J. In Organic Nitrogen Compounds II; 4th ed.; Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1991; Vol. E16b, p 24.
41. (f) Pfister, J. R. Synthesis 1984, 969.
42. (g) Okada, I.; Ichimura, K.; Sudo, R. Bull. Chem. Soc., Japan 1970, 43, 1185.
43. Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145.
44. Nakajima, K.; Kawai, H.; Takai, M.; Okawa, K. Bull. Chem. Soc., Japan 1977, 50, 917.
45. (a) Corrie, J. E.; Kirby, G. W.; Mackinnon, J. W. M. J. Chem. Soc., Perkin Trans 1 1985, 883.
46. (b) Kirby, G. W.; Sweeney, J. G. J. Chem. Soc., Chem. Comm. 1973, 704.
47. (c) Kirby, G. W. Chem. Soc. Rev. 1977, 1.
48. Boger, D. L.; Weinreb, S. L. Hetero Diels-Alder Methodology in Organic Synthesis.; Academic Press: San Diego, 1987.
49. (a) Kibayashi, C.; Aoyagi, S. Synlett 1995, 873.
50. (b) Streith, J.; Defoin, A. Synthesis 1994, 1107.
51. (c) Hudlicky, T.; Olivo, H. P.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5108.
52. (d) Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992, 114, 9694.
53. (e) Hudlicky, T.; Olivo, H. F. Tetrahedron Lett. 1991, 32, 6077.
54. (a) Keck, G. E.; Fleming, S.; Nickell, D.; Weider, P. Synth. Commun. 1979, 9, 281.
55. (b) Keck, G. E.; McHardy, S. F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419.
56. (a) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602.
57. (b) Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351.
58. 3-Bromo-1,2-dihydroxycyclohexa-3,5-diene was obtained as a gift from Prof. Tomas Hudlicky (University of Florida). See ref. 15c-e for examples of the addition of nitroso derivatives to this chiral diene.
59. Mitsunobu, O. Synthesis 1981, 1.
60. 3 271.1208, found 271.1202.