Asymmetric trisubstituted aziridination of aldimines and ketimines using N-α-Diazoacyl camphorsultams

Chemistry - An Asian Journal

Volumn 6, Issue 2, 2011, Pages 607-613

  Hashimoto, Takuya ^a   Nakatsu, Hiroki ^a   Yamamoto, Kumiko ^a   Watanabe, Shogo ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

asymmetric synthesis; aziridine; camphorsultam; chiral auxiliaries; diazo compounds

Indexed keywords

ASYMMETRIC SYNTHESIS; AZIRIDINES; CAMPHORSULTAM; CHIRAL AUXILIARIES; DIAZO COMPOUNDS;

CATALYSIS; ESTERS; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

EID: 79251514298     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000604     Document Type: Article

References (41)

1. E. N. Jacobsen, in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999, p. 607
2. Aziridines and Epoxides in Organic Synthesis (Ed.:, A. K. Yudin,), Wiley-VCH, Weinheim, Germany, 2006
3. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905
4. J. Sweeney, Eur. J. Org. Chem. 2009, 4911.
5. L. Casarrubios, J. A. Pérez, M. Brookhart, J. L. Templeton, J. Org. Chem. 1996, 61, 8358.
6. A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 1612.
7. J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099
8. J. C. Antilla, W. D. Wulff, Angew. Chem. 2000, 112, 4692
9. Angew. Chem. Int. Ed. 2000, 39, 4518
10. C. Loncaric, W. D. Wulff, Org. Lett. 2001, 3, 3675
11. A. P. Patwardhan, V. R. Pulgam, Y. Zhang, W. D. Wulff, Angew. Chem. 2005, 117, 6325
12. Angew. Chem. Int. Ed. 2005, 44, 6169
13. Z. Lu, Y. Zhang, W. D. Wulff, J. Am. Chem. Soc. 2007, 129, 7185
14. Y. Zhang, A. Desai, Z. Lu, G. Hu, Z. Ding, W. D. Wulff, Chem. Eur. J. 2008, 14, 3785
15. Y. Zhang, Z. Lu, A. Desai, W. D. Wulff, Org. Lett. 2008, 10, 5429
16. Y. Zhang, Z. Lu, W. D. Wulff, Synlett 2009, 2715.
17. Their recent study revealed that the catalyst actually acts as a chiral Brønsted acid, see;, G. Hu, L. Huang, R. H. Huang, W. D. Wulff, J. Am. Chem. Soc. 2009, 131, 15615.
18. For other chiral Lewis acid catalyzed reactions, see
19. K. Juhl, R. G. Hazell, K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 1 1999, 2293
20. M. Redlich, M. M. Hossain, Tetrahedron Lett. 2004, 45, 8987
21. P. Wipf, M. A. Lyon, ARKIVOC 2007, xii, 91.
22. T. Hashimoto, N. Uchiyama, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 14380.
23. X. Zeng, X. Zeng, Z. Xu, M. Lu, G. Zhong, Org. Lett. 2009, 11, 3036.
24. T. Akiyama, T. Suzuki, K. Mori, Org. Lett. 2009, 11, 2445.
25. T. Hashimoto, H. Nakatsu, S. Watanabe, K. Maruoka, Org. Lett. 2010, 12, 1668.
26. For the use of α-substituted α-diazocarbonyl compounds in acid-catalyzed stereoselective synthesis, see
27. T. Hashimoto, Y. Naganawa, T. Kano, K. Maruoka, Chem. Commun. 2007, 5143
28. T. Hashimoto, Y. Naganawa, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 2434
29. T. Hashimoto, Y. Naganawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 6614
30. T. Hashimoto, H. Miyamoto, Y. Naganawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 11280.
31. C. Tomasini, A. Vecchione, Org. Lett. 1999, 1, 2153.
32. For recent reviews on asymmetric synthesis of α,α- disubstituted α-amino acids, see
33. Y. Ohfune, T. Shinada, Eur. J. Org. Chem. 2005, 5127
34. H. Vogt, S. Bräse, Org. Biomol. Chem. 2007, 5, 406
35. C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 2007, 18, 569
36. R. A. Mosey, J. S. Fisk, J. J. Tepe, Tetrahedron: Asymmetry 2008, 19, 2755.
37. T. Hashimoto, Y. Naganawa, K. Maruoka, Chem. Commun. 2010, 46, 6810.
38. Manuscript in preparation.
39. For the determination of the stereochemistry, see the Supporting Information.
40. A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964.
41. A. L. Tillman, J.-X. Ye, D. J. Dixon, Chem. Commun. 2006, 1191.