Intramolecular nucleophilic deselenenylation reactions promoted by benzeneselenenyl triflate. Stereospecific synthesis of vicinal amino alcohol precursors

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7085-7091

  Tingoli, Marco ^a,b   Testaferri, Lorenzo ^a   Temperini, Andrea ^a   Tiecco, Marcello ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000503454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960866g     Document Type: Article

References (52)

1. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
2. Liotta, D. Organoselenium Chemistry; Wiley: New York, 1987.
3. Patai, S. The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, 1987, Vol. 1 and 2.
4. Tiecco, M.; Tingoli, M.; Testaferri, L. Pure Appl. Chem. 1993, 65, 715.
5. Barton, D. H. R.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1982, 23, 4949. For a detailed study: Back, T. G.; Birss, V. I.; Edwards, M.; Krishna, M. V. J. Org. Chem. 1988, 53, 3815.
6. Barton, D. H. R.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1982, 23, 4949. For a detailed study: Back, T. G.; Birss, V. I.; Edwards, M.; Krishna, M. V. J. Org. Chem. 1988, 53, 3815.
7. 3H: Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Menchen, S. M.; Russel, C. G.; Singh, A.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438.
8. 3H: Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Menchen, S. M.; Russel, C. G.; Singh, A.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438.
9. Keck, G. E.; Jates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
10. Tiecco, M. Synthesis 1988, 10, 749.
11. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697. Other early reports are: Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1973, 695.
12. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697. Other early reports are: Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1973, 695.
13. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697. Other early reports are: Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1973, 695.
14. Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784. For detailed studies: Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697; Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
15. Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784. For detailed studies: Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697; Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
16. Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784. For detailed studies: Reich, H. J.; Wollowitz, S.; Trend, J. E.; Chow, F.; Wendelborn, D. F. J. Org. Chem. 1978, 43, 1697; Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
17. Tiecco, M.; Testaferri, L.; Tingoli, M.; Marini, F. J. Org. Chem. 1993, 58, 1349.
18. Sharpless, K. B.; Lauer, R. F. J Am. Chem. Soc. 1972, 94, 7154.
19. Tiecco, M.; Chianelli, D.; Testaferri, L.; Tingoli, M.; Bartoli, D. Tetrahedron 1986, 42, 4889.
20. Krief, A.; Dumont, W.; Denis, J. N. J. Chem. Soc., Chem. Commun. 1985, 571. Nearly simultaneous work: Uemura, S.; Fukuzawa, S.-I. J. Chem Soc., Perkin Trans, 1 1985, 471.
21. Krief, A.; Dumont, W.; Denis, J. N. J. Chem. Soc., Chem. Commun. 1985, 571. Nearly simultaneous work: Uemura, S.; Fukuzawa, S.-I. J. Chem Soc., Perkin Trans, 1 1985, 471.
22. Sevrin, M.; Krief, A. J. Chem. Soc., Chem. Commun. 1980, 656.
23. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. Tetrahedron 1988, 44, 2261.
24. Tingoli, M.; Tiecco, M.; Testaferri, L.; Temperini, A. J. Chem. Soc., Chem. Commun. 1994, 1883.
25. Murata, S.; Suzuki, T. Chem. Lett. 1987, 849. Nearly simultaneous work: Okazaki, R.; Itoh, Y. Chem. Lett. 1987, 1575.
26. Murata, S.; Suzuki, T. Chem. Lett. 1987, 849. Nearly simultaneous work: Okazaki, R.; Itoh, Y. Chem. Lett. 1987, 1575.
27. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809.
28. Clive, D. L. J.; Farina, V.; Sinigh, A.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. Chem. Soc., Chem. Commun. 1978, 379.
29. Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D.; Balducci, R. J. Org. Chem. 1990, 55, 429.
30. Clive, D. L. J.; Farina, V.; Sinigh, A.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. Org. Chem. 1980, 45, 2120.
31. Webb II, R. R.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 1357.
32. Toshimitsu, A.; Terao, K.; Uemura, S. J. Org. Chem. 1986, 51, 1724.
33. Cooper, M. A.; Ward, A. D. Tetrahedron Lett. 1994, 35, 5065.
34. Tingoli, M.; Tiecco, M.; Testaferri, L.; Andrenacci, R.; Balducci, R. J. Org. Chem. 1993, 58, 6097. There are more general references on how "the azido group can be used to effect several conversions leading to the formation of more complex molecules". For example, Patai, S. The Chemistry of the Azido Group, Wiley: London, 1971.
35. Tingoli, M.; Tiecco, M.; Testaferri, L.; Andrenacci, R.; Balducci, R. J. Org. Chem. 1993, 58, 6097. There are more general references on how "the azido group can be used to effect several conversions leading to the formation of more complex molecules". For example, Patai, S. The Chemistry of the Azido Group, Wiley: London, 1971.
36. Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
37. (a) Giuliano, R. M.; Bigos, C. Synth. Commun. 1995, 25, 1145.
38. (b) Li, C.; Fuchs, P. L. Synlett 1994, 629.
39. (c) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1987, 28, 6331.
40. (d) Hassner, A.; Lorber, M. E.; Heathcock, C. J. Org. Chem. 1967, 32, 540.
41. Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. J. Org. Chem. 1981, 46, 4727.
42. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. Tetrahedron Lett. 1989, 30, 1417.
43. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
44. Dewar, M. J. S.; Fahey, R. C. J Am. Chem. Soc. 1963, 85, 2245.
45. (a) Denis, J. N.; Vicens, J.; Krief, A. Tetrahedron Lett. 1979, 2697.
46. (b) Hassner, A.; Amarasekara, A. S. Tetrahedron Lett. 1987, 28, 5185.
47. Olsen, R. K.; Bhat, K. L.; Wardle, R. B.; Hennen, W. J.; Kini, G. D. J. Org. Chem. 1985, 50, 896.
48. Yoshida, M.; Satoh, N.; Kamigata, N. Chem. Lett. 1989, 1433.
49. Padwa, A.; Gasdaska, J. R; Tomas, M.; Turro, N. J.; Cha, Y.; Gould, I. R. J. Am. Chem. Soc. 1986, 108, 6739.
50. Bellucci, G.; Bianchini, R.; Chiappe, C. J. Org. Chem. 1991, 56, 3067.
51. Hu, N. X.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1888, 29, 1049.
52. Hu, N. X.; Aso, Y.; Oteubo, T.; Ogura, F. J. Chem. Soc., Chem. Commun. 1987, 1447.