Scandium triflate catalyzed aminolysis of meso-aziridines

Synlett

Volumn , Issue 14, 2007, Pages 2289-2291

  Peruncheralathan, Saravanan ^a   Henze, Michael ^a   Schneider, Christoph ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

1,2 diamine; Amine; Aziridine; Catalysis; Scandium

Indexed keywords

1,2 DIAMINE DERIVATIVE; AZIRIDINE DERIVATIVE; BIPYRIDINE; DIAMINE DERIVATIVE; INDIUM; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 34548733591     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984920     Document Type: Article

References (39)

1. Reviews: (a) Schneider, C. Synthesis 2006, 3919.
2. (b) Pastor, I. M.; Yus, M. Curr. Org. Chem. 2005, 9, 1.
3. (c) Jacobsen, E. N.; Wu, M. H. Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 649.
4. Reviews: (a) Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
5. (b) Pineschi, M. Eur. J. Org. Chem. 2006, 4979.
6. (c) Hu, X. E. Tetrahedron 2004, 60, 2701.
7. (d) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
8. For select catalytic processes, see: (a) Wu, J.; Sun, X.; Li, Y. Eur. J. Org. Chem. 2005, 4271.
9. (b) Bisai, A.; Bhanu Prasad, B. A.; Singh, V. K. Tetrahedron Lett. 2005, 46, 7935.
10. (c) Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 68, 5160.
11. (d) Swamy, N. R.; Venkateswarlu, Y. Synth. Commun. 2003, 33, 547.
12. (e) Yadav, J. S.; Reddy, B. V. S.; Rao, K. V.; Raj, K. S.; Prasad, A. R. Synthesis 2002, 1061.
13. (f) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J. R. Synthesis 2002, 2211.
14. (g) Hou, X.-L.; Fan, R.-H.; Dai, L.-X. J. Org. Chem. 2002, 67, 5295.
15. (h) Chandrasekhar, M.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 10079.
16. (i) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
17. (j) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395.
18. For select catalytic processes, see: (a) Bhanu Prasad, B. A.; Sanghi, R.; Singh, V. K. Tetrahedron 2002, 58, 7355.
19. (b) Hou, X.-L.; Fan, R.-H.; Dai, L.-X. J. Org. Chem. 2002, 67, 5295.
20. (c) Bhanu Prasad, B. A.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 4677.
21. For select catalytic processes, see: (a) Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Venkatram Reddy, P.; Narsaiah, A. V. Catal. Commun. 2006, 7, 807.
22. (b) Wu, J.; Sun, X.; Li, Y. Eur. J. Org. Chem. 2005, 4271.
23. (c) Yadav, J. S.; Subba Reddy, B. V.; Baishya, G.; Reddy, P. V.; Harshavardhan, S. J. Synthesis 2004, 1854.
24. (d) Hou, X.-L.; Fan, R.-H.; Dai, L.-X. J. Org. Chem. 2002, 67, 5295.
25. (e) Wu, J.; Hou, X.-L.; Dai, L.-X. J. Chem. Soc., Perkin Trans. 1 2001, 1314.
26. (f) Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 2699.
27. (g) For the first catalytic, enantioselective process, see: Luo, Z.-B.; Hou, X.-L.; Dai, L.-X. Tetrahedron: Asymmetry 2007, 18, 443.
28. (a) Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
29. (b) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
30. (c) For previous catalytic, enantioselective azide addition to meso-aziridines, see: Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
31. (a) Schneider, C.; Sreekanth, A. R.; Mai, E. Angew. Chem. Int. Ed. 2004, 43, 5691;
32. Angew. Chem. 2004, 116, 5809.
33. (b) Mai, E.; Schneider, C. Chem. Eur. J. 2007, 13, 2729.
34. (c) Tschöp, A.; Marx, A.; Sreekanth, A. R.; Schneider, C. Eur. J. Org. Chem. 2007, 2318.
35. (d) Nandakumar, M. V.; Tschöp, A.; Krautscheid, H.; Schneider, C. Chem. Commun. 2007, 2756.
36. (e) Mai, E.; Schneider, C. Synlett 2007, 2136.
37. Scandium triflate has been shown to catalyze the addition of acid anhydrides to aziridines, see: Yadav, J. S.; Reddy, B. V. S.; Sadashiv, K.; Harikishan, K.; Narsaiah, A. V. J. Mol. Catal. A: Chem. 2004, 220, 153.
38. Ferraris, D.; Drury, W. J. III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
39. 2 (5 mL), were added N-phenyl aziridine (1.00 mmol) and amine (1.50 mmol), and the mixture was stirred at r.t. for 1 h (monitored by TLC). The solvent was removed in vacuo and the crude product was purified through flash chromatography using pentane-EtOAc (15:1) as eluent. For analytical and spectroscopic details of the products see ref. 3.