Reductive alkylation of β-alkoxy aziridines: New route to substituted allylic amines

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4817-4819

  Rosser, Clare M ^a   Coole, Susannah C ^a   Kirby, Jonathan P ^a   O'Brien, Peter ^a   Caine, Darren ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; AZIRIDINE DERIVATIVE; LITHIUM DERIVATIVE;

ALKYLATION; ARTICLE; BROMINATION; CIS TRANS ISOMERISM; ELIMINATION REACTION; METHYLATION; NUCLEAR OVERHAUSER EFFECT; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY;

ALKYLATION; ALLYL COMPOUNDS; AMINES; AZIRIDINES; CATALYSIS; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 12344264796     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048201l     Document Type: Article

References (36)

1. (a) Satoh, T. Chem. Rev. 1996, 96, 3303.
2. (b) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337.
3. (c) Hodgson, D. M. Gras, E. Synthesis 2002, 1625.
4. (d) For a special issue of Tetrahedron on oxiranyl and aziridinyl anions, see: Tetrahedron 2003, 9693-9847.
5. For recent examples, see: (a) Capriati, V.; Florio, S.; Luisi, R.; Nuzzo, I. J. Org. Chem. 2004, 69, 3330. (b) Hodgson, D. M.; Paruch, E. Tetrahedron 2004, 60, 5185.
6. For recent examples, see: (a) Capriati, V.; Florio, S.; Luisi, R.; Nuzzo, I. J. Org. Chem. 2004, 69, 3330. (b) Hodgson, D. M.; Paruch, E. Tetrahedron 2004, 60, 5185.
7. (a) Beak, P.; Wu, S.; Yum, E. K.; Jun, Y. M. J. Org. Chem. 1994, 59, 276.
8. (b) Yamauchi, Y.; Kawate, T.; Katagiri, T.; Uneyama, K. Tetrahedron 2003, 59, 9839.
9. (c) Vedejs, E.; Bhanu Prasad, A. S.; Kendall, J. T.; Russel, J. S. Tetrahedron 2003, 59, 9849.
10. (d) Müller, P.; Riegert, D.; Bernardinelli, G. Helv. Chim. Acta 2004, 87, 227.
11. O'Brien, P.; Rosser, C. M.; Caine, D. Tetrahedron Lett. 2003, 44, 6613.
12. O'Brien, P.; Rosser, C. M.; Caine, D. Tetrahedron 2003, 59, 9779.
13. (a) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526.
14. (b) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4527.
15. Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943.
16. Dechoux, L.; Doris, E.; Mioskowski, C. Chem. Commun. 1996, 549.
17. (a) Hodgson, D. M.; Stent, M. A. H.; Wilson, F. X. Org. Lett. 2001, 3, 3401.
18. (b) Hodgson, D. M.; Stent, M. A. H.; Wilson, F. X. Synthesis 2002, 1445.
19. (c) Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Matthews, I. R.; Witherington, J. Tetrahedron 2004, 60, 3611.
20. A similar strategy using dihydrofuran aziridine and aziridines of acyclic allylic ethers has recently been disclosed: Hodgson, D. M.; Stefane, B.; Miles, T. J.; Witherington, J. Chem. Commun. 2004, 2234.
21. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
22. (a) Caine, D.; O'Brien, P.; Rosser, C. M. Org. Lett. 2002, 4, 1923.
23. (b) Schmitt, A. C.; Smith, C. M.; Voight, E. A.; O'Doherty, G. A. Heterocycles 2003, 62, 635.
24. (c) Armstrong, A.; Cumming, G. R.; Pike, K. Chem. Commun. 2004, 812.
25. 2Et keto aziridines have been prepared using other routes. See: (a) Fioravanti, S.; Pellacani, L.; Tabanella, S.; Tardella, P. A. Tetrahedron 2003, 54, 14105. (b) Barros, M. T.; Maycock, C. D.; Ventura, M. R. Tetrahedron Lett. 2002, 43, 4329.
26. 2Et keto aziridines have been prepared using other routes. See: (a) Fioravanti, S.; Pellacani, L.; Tabanella, S.; Tardella, P. A. Tetrahedron 2003, 54, 14105. (b) Barros, M. T.; Maycock, C. D.; Ventura, M. R. Tetrahedron Lett. 2002, 43, 4329.
27. (a) Sepúlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, 233.
28. (b) Sepúlveda, J.; Soriano, C.; Mestres, R.; Sendra, J. Bull. Soc. Chim. Fr. 1983, 241.
29. (c) Sepúlveda, J.; Soriano, C.; Roquet-Jalmar, J.; Mestres, R.; Riego, J. Bull. Soc. Chim. Fr. 1987, 189.
30. (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N.; Chounan, Y.; Yamamoto, Y. J. Org. Chem. 1995, 60, 2044.
31. (b) Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinet, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726.
32. (a) O'Brien, P.; Childs, A. C.; Ensor, G.; Hill, C. L. Kirby, J. P.; Dearden, M. J.; Oxenford, S.; Rosser, C. M. Org. Lett. 2003, 5, 4955.
33. (b) Bäckvall, J.-E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1979, 44, 1953.
34. The isolation of an ene-sulfonamide from the reaction of N-tosyl cyclohexeneaziridine with sec-butyllithium and (-)-sparteine has been described previously. See: Müller, P.; Nury, P. Helv. Chim. Acta 2001, 84, 662. However, isolation of the ene-sulfonamide could not be reproduced by the same group; see ref 3d.
35. (a) Doris, E.; Dechoux, L.; Mioskowski, C. J. Am. Chem. Soc. 1995, 117, 12700.
36. (b) Doris, E.; Mioskowski, C.; Dechoux, L.; Agami, C. J. Org. Chem. 1998, 63, 3808.