Novel synthesis of chiral unactivated 2-aryl-1-benzylaziridines

Synlett

Volumn , Issue 8, 2009, Pages 1265-1268

  Leemans, Erika ^a   Mangelinckx, Sven ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Asymmetric synthesis; Chiral aziridines; Haloimines; Ring closure; Ring opening

Indexed keywords

ACID; AMINE; AZIRIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DEPROTECTION REACTION; ENANTIOMER; INFORMATION CENTER; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SYNTHESIS;

EID: 67649363684     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088125     Document Type: Article

References (55)

1. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
2. For selected examples with N-nucleophiles, see: (a) Karikomi, M.; De Kimpe, N. Tetrahedron Lett. 2000, 41, 10295.
3. (b) D'hooghe, M.; Van Speybroeck, V.; Van Nieuwenhove, A.; Waroquier, M.; De Kimpe, N. J. Org. Chem. 2007, 72, 4733.
4. For a recent example of enzymatic resolution of unactivated aziridines and their study in nucleophilic ring opening reactions, see: Moran-Ramallal, R.; Liz, R.; Gotor, V. Org. Lett. 2007, 9, 521.
5. (a) Gabriel, S. Ber. Dtsch. Chem. Ges. 1888, 21, 1049.
6. (b) Wenker, H. J. Am. Chem. Soc. 1935, 57, 2328.
7. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
8. Sinou, D.; Emziane, M. Tetrahedron Lett. 1986, 27, 4423.
9. (a) Sweeney, J. B.; Cantrill, A. A.; Drew, M. G. B.; McLaren, A. B.; Thobhani, S. Tetrahedron 2006, 62, 3694.
10. (b) Sweeney, J. B.; Cantrill, A. A.; McLaren, A. B.; Thobhani, S. Tetrahedron 2006, 62, 3681.
11. (c) Kim, D. Y.; Suh, K. H.; Choi, J. S.; Mang, J. Y.; Chang, S. K. Synth. Commun. 2000, 30, 87.
12. (d) Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. Chem. Commun. 1996, 2631.
13. (a) Atkinson, R. S.; Coogan, M. P.; Lochrie, I. S. T. Chem. Commun. 1996, 789.
14. (b) Roth, P.; Somfai, P.; Andersson, P. G. Chem. Commun. 2002, 1752.
15. (c) Sjöholm-Timén, Å.; Somfai, P. J. Org. Chem. 2003, 68, 9958.
16. (d) Risberg, E.; Andreas, F. B.; Somfai, P. Chem. Commun. 2004, 2088.
17. (e) Risberg, E.; Fischer, A.; Somfai, P. Tetrahedron 2005, 61, 8443.
18. (a) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194.
19. (b) Ma, L.; Jiao, P.; Zhang, Q.; Xu, J. Tetrahedron: Asymmetry 2005, 16, 3718.
20. (c) Atkinson, R. S.; Tughan, G. J. Chem. Soc., Chem. Commun. 1987, 456.
21. (a) Bilke, J. L.; Dzuganova, M.; Fröhlich, R.; Würthwein, E.-U. Org. Lett. 2005, 7, 3267.
22. (b) Bouyacoub, A.; Volatron, F. Eur. J. Org. Chem. 2002, 4143.
23. (c) Hudlicky, T.; Rinner, U.; Gonzalez, D.; Akgun, H.; Schilling, S.; Siengalewicz, P.; Martinot, T. A.; Pettit, G. R. J. Org. Chem. 2002, 67, 8726.
24. (d) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
25. (a) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2007, 72, 3211.
26. (b) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2008, 73, 5662.
27. (c) Denolf, B.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2006, 8, 3129.
28. (d) Denolf, B.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2007, 9, 187.
29. (e) Malkov, A. V.; Stončius, S.; Kočovský, P. Angew. Chem. Int. Ed. 2007, 46, 3722.
30. (f) Hodgson, D. M.; Kloesges, J.; Evans, B. Org. Lett. 2008, 10, 2781.
31. (g) Chen, Q.; Li, J.; Yuan, C. Synthesis 2008, 2986.
32. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
33. (a) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
34. (b) Hu, X. E. Tetrahedron 2004, 60, 2701.
35. (a) Cossy, J.; Bellosta, V. FR 2821354, 2002, Chem. Abstr. 2003, 138, 169957.
36. (b) Allan, R. D.; Tran, H. W. Aust. J. Chem. 1990, 43, 1123.
37. (c) Ghorai, M. K.; Das, K.; Shukla, D. J. Org. Chem. 2007, 72, 5859.
38. (d) Ghorai, M. K.; Ghosh, K. Tetrahedron Lett. 2007, 48, 3191.
39. (e) Ghorai, M. K.; Das, K.; Kumar, A.; Ghosh, K. Tetrahedron Lett. 2005, 46, 4103.
40. For some reviews on the importance of phenylethylamines, see: (a) Smith, T. A. Phytochemistry 1977, 16, 9.
41. (b) Juaristi, E.; Léon-Romo, J. L.; Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441.
42. (c) Juaristi, E.; Escalante, J.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1998, 9, 715.
43. (d) Bentley, K. W. Nat. Prod. Rep. 2006, 23, 444.
44. 19NOS: C, 65.78; H, 8.07; N, 5.90; S, 13.51. Found: C, 65.44; H, 8.35; N, 6.11; S, 13.28.
45. 2: C, 52.45; H, 6.36; N, 6.80. Found: C, 52.52; H, 6.42; N, 6.57.
46. 16NCl: C, 74.55; H, 6.26; N, 5.43. Found: C, 74.89; H, 6.37; N, 5.20.
47. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384.
48. Ema, T.; Tamida, D.; Sahai, T. J. Am. Chem. Soc. 2007, 129, 10591.
49. N2 pathway, see ref. 14c-e.
50. (a) Galindo, A.; Orea, L. F.; Gnecco, D.; Enriquez, R. G.; Toscano, R. A.; Reynolds, W. F. Tetrahedron: Asymmetry 1997, 8, 2877.
51. (b) Van, N. T.; De Kimpe, N. Tetrahedron 2000, 56, 7299.
52. 17N: C, 86.05; H, 7.67; N, 6.27. Found: C, 86.21; H, 7.83; N, 5.96.
53. Tsuchiya, Y.; Kumamoto, T.; Ishikawa, T. J. Org. Chem. 2004, 69, 8504.
54. (a) Kawamoto, A. M.; Wills, M. Tetrahedron: Asymmetry 2000, 11, 3257.
55. (b) Kawamoto, A. M.; Wills, M. J. Chem. Soc., Perkin Trans. 1 2001, 1916.