Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: An efficient route to 1,2-azido alcohols

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4261-4264

  Kamal, Ahmed ^a   Arifuddin, M ^a   Rao, Maddamsetty V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BETA CYCLODEXTRIN; EPOXIDE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033388823     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00464-4     Document Type: Article

References (34)

1. (a) Erden, I. In Comprehensive Heterocyclic Chemistry; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. IA, Chapter 1.03.
2. (b) Bartok, M.; Lang, K. L. In Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1985; Vol. 42, part 3, p. 1.
3. Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361 and references cited therein.
4. (a) Birkofer, I.; Kaiser, W. Liebigs Ann. Chem. 1975, 266.
5. (b) Blandy, C.; Choukroun, R.; Gervais, D. Tetrahedron Lett. 1983, 24, 4189.
6. (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560.
7. (d) Maruoka, K.; Sano, H.; Yamamoto, H. Chem. Lett. 1985, 599.
8. (e) Sinou, D.; Emziane. M. Tetrahedron Lett. 1986, 27, 4423.
9. (f) Caron, M.; Carlier, P. R.; Sharpless, K. B. J. Org. Chem. 1988, 53, 5185.
10. (g) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768.
11. (h) For a recent review, see: Paterson, I.; Berrisford, D. J. In Organic Synthesis Highlights III; Mulzer, J.; Waldmann, H., Eds.; Wiley-VCH, 1998.
12. (a) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
13. (b) Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389.
14. (c) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
15. (d) Annis, D. A.; Helluim, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1907.
16. Hou, X.-L.; Wu, J.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. Tetrahedron: Asymmetry 1998, 9, 1747.
17. (a) Kamal, A.; Rao, A. B.; Rao, M. V. Tetrahedron Lett. 1992, 33, 4077.
18. (b) Kamal, A.; Damayanthi, Y.; Rao, M. V. Tetrahedron: Asymmetry 1992, 3, 1361.
19. (c) Kamal, A.; Rao, M. V. Tetrahedron: Asymmetry 1994, 5, 1881.
20. Hu, Y.; Uno, M.; Harada, A.; Takahashi, S. Chem. Lett. 1990, 797 and references cited therein.
21. (a) Tabushi, I. Acc. Chem. Res. 1982, 15, 66.
22. (b) Breslow, R.; Campbell, P. Bioorg. Chem. 1971, 1, 140.
23. (c) Komiyama, M.; Hirai, H. J. Am. Chem. Soc. 1984, 106, 74.
24. (d) Sakuraba, H.; Inomata, N.; Tanaka, Y. J. Org. Chem. 1989, 54, 3482.
25. (e) Hu, Y.; Harada, A.; Takahashi, S. Synth. Commun. 1988, 18, 1607.
26. (f) Banfi, S.; Colonna, S.; Julia, S. Synth. Commun. 1983, 13, 1049.
27. For recent reviews on cyclodextrin, see: (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
28. (b) Takahashi, K. Chem. Rev. 1998, 98, 2013.
29. (a) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213.
30. (b) Sutowardoyo, K. I.; Emziane, M.; Lhoste, P.; Sinou, D. Tetrahedron 1991, 47, 1435.
31. (c) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 774.
32. (d) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 1021.
33. (e) Crotti, P.; Bussolo, V. D.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1996, 37, 1675.
34. Ader, U.; Muschalek, V.; Schneider, M. P. Chirality 1993, 5, 554.