Diastereocontrolled Synthesis of trans- and cis-meso-Cyclopentene Aziridines

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1923-1926

  Caine, Darren ^a   O'Brien, Peter ^b   Rosser, Clare M ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0012218712     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0259387     Document Type: Article

References (32)

1. For reviews, see: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
2. For reviews, see: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
3. For reviews, see: Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron 1996, 52, 14361. Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
4. For recent examples of this strategy in synthesis, see: Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron Lett. 2001, 42, 8081.
5. For recent examples of this strategy in synthesis, see: Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441. de Sousa, S. E.; O'Brien, P.; Pilgram, C. D. Tetrahedron Lett. 2001, 42, 8081.
6. da Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
7. Li, Z.; Fernández, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
8. Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. Tetrahedron 1996, 52, 7817.
9. Müller, P.; Nury. P. Helv. Chim. Acta 2001, 84, 662.
10. Zalkow, L. H.; Hill, R. H. Tetrahedron 1975, 31, 831. Gassman, P. G.; Schaffhausen, J. G. J. Org. Chem. 1978, 43, 3241. Schoenfeld, R. C.; Lumb, J.-P.; Ganem, B. Tetrahedron Lett. 2001, 42, 6447.
11. Zalkow, L. H.; Hill, R. H. Tetrahedron 1975, 31, 831. Gassman, P. G.; Schaffhausen, J. G. J. Org. Chem. 1978, 43, 3241. Schoenfeld, R. C.; Lumb, J.-P.; Ganem, B. Tetrahedron Lett. 2001, 42, 6447.
12. Zalkow, L. H.; Hill, R. H. Tetrahedron 1975, 31, 831. Gassman, P. G.; Schaffhausen, J. G. J. Org. Chem. 1978, 43, 3241. Schoenfeld, R. C.; Lumb, J.-P.; Ganem, B. Tetrahedron Lett. 2001, 42, 6447.
13. O'Brien, P.; Pilgram, C. D. Tetrahedron Lett. 1999, 40, 8427.
14. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783. For a different ammonium salt used in the same type of aziridination protocol, see: Ali, S. I.; Nikalje, M. D.; Sudulai, A. Org. Lett. 1999, 1. 705.
15. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783. For a different ammonium salt used in the same type of aziridination protocol, see: Ali, S. I.; Nikalje, M. D.; Sudulai, A. Org. Lett. 1999, 1. 705.
16. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Gontcharov, A. V.; Liu, H.; Sharpless, K. B. Org. Lett. 1999, 1, 783. For a different ammonium salt used in the same type of aziridination protocol, see: Ali, S. I.; Nikalje, M. D.; Sudulai, A. Org. Lett. 1999, 1. 705.
17. Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
18. Söndergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897.
19. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
20. For examples of diastereoselective aziridination reactions using PhI= NTs, see: Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. White, R. D.; Wood, J. L. Org. Lett. 2001, 3, 1825.
21. For examples of diastereoselective aziridination reactions using PhI= NTs, see: Hudlicky, T.; Tian, X.; Königsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. White, R. D.; Wood, J. L. Org. Lett. 2001, 3, 1825.
22. For examples of diastereoselective aziridination reactions not involving iodinanes, see: Fioravanti. S.; Luna, G.; Pellacani, L.; Tardella, P. A. Tetrahedron 1997, 53, 4779. Atkinson, R. S.; Kelly, B. J. Chem. Commun. 1998, 624.
23. For examples of diastereoselective aziridination reactions not involving iodinanes, see: Fioravanti. S.; Luna, G.; Pellacani, L.; Tardella, P. A. Tetrahedron 1997, 53, 4779. Atkinson, R. S.; Kelly, B. J. Chem. Commun. 1998, 624.
24. Crandall, J. K.; Banks, D. B.; Coyler, A.; Watkins, R. J.; Arrington, J. P. J. Org. Chem. 1968, 33, 423.
25. 2O).
26. Asami, M. Bull. Chem. Soc. Jpn. 1990, 63, 1402.
27. H 4.36-4.41.
28. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
29. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. Nihei, K-i.; Kato, M. J.; Yamane, T.; Palma, M. S.; Konno, K. Synlett 2001, 1167.
30. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. Nihei, K-i.; Kato, M. J.; Yamane, T.; Palma, M. S.; Konno, K. Synlett 2001, 1167.
31. Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 30, 5253.
32. For an example of a hydroxyl-directed aziridination, see: Atkinson, R. S.; Kelly, B. J. J. Chem. Soc., Perkin Trans. 1 1989, 1515.