Catalytic asymmetric 1,3-dipolar cycloaddition of two different ylides: Facile access to chiral 1,2,4-triazinane frameworks

Angewandte Chemie - International Edition

Volumn 52, Issue 47, 2013, Pages 12377-12380

  Tong, Min Chao ^a   Chen, Xuan ^a   Tao, Hai Yan ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

asymmetric catalysis; azomethine ylide; copper; cycloaddition; heterocycles

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; ASYMMETRIC CATALYSIS; AZOMETHINE YLIDES; CATALYTIC SYSTEM; DIASTEREOSELECTIVITIES; FUNCTIONALIZED; HETEROCYCLES; MILD REACTION CONDITIONS;

CHEMICAL REACTIONS; CHEMISTRY; COPPER;

CYCLOADDITION;

1,2,4 TRIAZINE; 1,2,4-TRIAZINE; AZO COMPOUND; AZOMETHINE; AZOMETHINE YLIDE; COORDINATION COMPOUND; COPPER; THIOSEMICARBAZONE DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMISTRY; CONFORMATION; CYCLOADDITION; HETEROCYCLES; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ASYMMETRIC CATALYSIS; AZOMETHINE YLIDE; COPPER; CYCLOADDITION; HETEROCYCLES;

AZO COMPOUNDS; CATALYSIS; COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; MOLECULAR CONFORMATION; STEREOISOMERISM; THIOSEMICARBAZONES; TRIAZINES;

EID: 84887515262     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306300     Document Type: Article

References (61)

1. X.-L. Hou, Z. Yang, K.-S. Yeung, H. N. C. Wong, in Progress in Heterocyclic Chemistry, Vol.19 (Eds.:, G.W. Gribble, J. Joule,), Pergamon, Oxford, 2008
2. I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, Chem. Rev. 1996, 96, 635
3. L. Yet, Chem. Rev. 2000, 100, 2963
4. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813
5. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127
6. W. Zhao, Chem. Rev. 2010, 110, 1706
7. W. Carruthers, Cycloaddition Reactions in Organic Synthesis Pergamon, Oxford, 1990, pp. 1-208.
8. J. S. Bindra, R. H. F. Manske, The Alkaloids, Vol.14, Academic Press, New York, 1973
9. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
10. Angew. Chem. Int. Ed. 2007, 46, 8748.
11. L. Hong, R. Wang, Adv. Synth. Catal. 2013, 355, 1023.
12. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49
13. P. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791.
14. 1,3-Dipolar Cycloaddition Chemistry (Ed.:, A. Padwa,), Wiley, New York, 1984
15. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products (Ed.:, A. Padwa, W.H. Pearson,), Wiley, New York, 2003.
16. L. N. Jungheim, S. K. Sigmund, J. Org. Chem. 1987, 52, 4007
17. W. Duczek, H.-J. Niclas, Tetrahedron Lett. 1995, 36, 2457
18. Y. Xin, J.-W. Zhao, J.-W. Gu, S.-Z. Zhu, J. Fluorine Chem. 2011, 132, 402
19. N. D. Shapiro, Y. Shi, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 11654. Pyrazolidinium ylides were also named as azomethine imines in the literature.
20. R. Shintani, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 10778
21. A. Suárez, C. W. Downey, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 11244
22. W. Chen, X.-H. Yuan, R. Li, W. Du, Y. Wu, L.-S. Ding, Y.-C. Chen, Adv. Synth. Catal. 2006, 348, 1818
23. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811
24. Angew. Chem. Int. Ed. 2007, 46, 7667
25. H. Suga, A. Funyu, A. Kakehi, Org. Lett. 2007, 9, 97
26. M. P. Sibi, D. Rane, L. M. Stanley, T. Soeta, Org. Lett. 2008, 10, 2971
27. M. Keller, A. S. S. Sido, P. Pale, J. Sommer, Chem. Eur. J. 2009, 15, 2810
28. K. Yoshimura, T. Oishi, K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2011, 17, 3827
29. T. Imaizumi, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2012, 134, 20049
30. T. Hashimoto, Y. Maeda, M. Omote, H. Nakatsu, K. Maruoka, J. Am. Chem. Soc. 2010, 132, 4076
31. L. Hong, M. Kai, C. Wu, W. Sun, G. Zhu, G. Li, X. Yao, R. Wang, Chem. Commun. 2013, 49, 6713
32. R. Na, C. Jing, Q. Xu, H. Jiang, X. Wu, J. Shi, J. C. Zhong, M. Wang, D. Benitez, E. Tkatchouk, W. A. Goddard, H. C. Guo, O. Kwon, J. Am. Chem. Soc. 2011, 133, 13337
33. R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 6330
34. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334
35. Y. Qian, P. J. Zavalij, W. Hu, M. P. Doyle, Org. Lett. 2013, 15, 1564
36. C. Perreault, S. R. Goudreau, L. E. Zimmer, A. B. Charette, Org. Lett. 2008, 10, 689
37. X. Xu, Y. Qian, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2013, 135, 1244
38. J. Li, X. Lian, X. Liu, L. Lin, X. Feng, Chem. Eur. J. 2013, 19, 5134.
39. J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156
40. Q.-A. Chen, D.-S. Wang, Y.-G. Zhou, Chem. Commun. 2010, 46, 4043
41. J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784.
42. H. Dorn, T. Kreher, Tetrahedron Lett. 1988, 29, 2939
43. E. Erkizia, E. Aldaba, Y. Vara, A. Arrieta, H. Gornitzka, F. P. Cossío, ARKIVOC 2005, 189.
44. A. S. Oganisyan, G. O. Grigoryan, A. S. Noravyan, I. A. Dzhagatspanyan, G. G. Melikyan, Pharm. Chem. J. 2001, 35, 124
45. A. Deeb, F. El-Mariah, M. Hosny, Bioorg. Med. Chem. Lett. 2004, 14, 5013
46. T. E. Ali, Eur. J. Med. Chem. 2009, 44, 4539
47. D. Kaushik, S. A. Khan, G. Chawla, Eur. J. Med. Chem. 2010, 45, 3960
48. P. Zhan, X. Li, Z. Li, X. Chen, Y. Tian, W. Chen, X. Liu, C. Pannecouque, E. D. Clercq, Bioorg. Med. Chem. Lett. 2012, 22, 7155
49. M. Congreve, S. P. Andrews, A. S. Doré, K. Hollenstein, E. Hurrell, C. J. Langmead, J. S. Mason, I. W. Ng, B. Tehan, A. Zhukov, M. Weir, F. H. Marshall, J. Med. Chem. 2012, 55, 1898.
50. W. Li, J. Gan, D. Ma, Angew. Chem. 2009, 121, 9053
51. Angew. Chem. Int. Ed. 2009, 48, 8891
52. E. D. Miller, C. A. Kauffman, P. R. Jensen, W. Fenical, J. Org. Chem. 2007, 72, 323
53. G. Varvounis, Y. Fiamegos, G. Pilidis, Adv. Heterocycl. Chem. 2001, 80, 75.
54. H. Dorn, A. Otto, Chem. Ber. 1968, 101, 3287
55. H. Dorn, A. Otto, Angew. Chem. 1968, 80, 196
56. Angew. Chem. Int. Ed. Engl. 1968, 7, 214.
57. C. J. Richards, A. W. Mulvaney, Tetrahedron: Asymmetry 1996, 7, 1419.
58. CCDC 946767 (3 aa) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
59. X.-X. Yan, Q, Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, Y.-D. Wu, Angew. Chem. 2006, 118, 2013
60. Angew. Chem. Int. Ed. 2006, 45, 1979
61. W. Gao, X. Zhang, M. Raghunath, Org. Lett. 2005, 7, 4241.