Catalytic asymmetric 1,3-dipolar [3 + 6] cycloaddition of azomethine ylides with 2-Acyl cycloheptatrienes: Efficient construction of bridged heterocycles bearing piperidine moiety

Journal of the American Chemical Society

Volumn 136, Issue 24, 2014, Pages 8685-8692

  Li, Qing Hua ^a   Wei, Liang ^a   Wang, Chun Jiang ^a,b  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

AZOMETHINE; AZOMETHINE YLIDES; CYCLOHEPTATRIENES; DIPOLAROPHILES; EFFICIENT CONSTRUCTION; HETEROCYCLES; KEY FACTORS;

CHEMISTRY;

AROMATIC COMPOUND; AZOMETHINE YLIDE; COPPER COMPLEX; CYCLOHEPTATRIENE; ESTER; HETEROCYCLIC COMPOUND; PIPERIDINE; UNCLASSIFIED DRUG; AZO COMPOUND; AZOMETHINE; CYCLOHEPTANE DERIVATIVE; ORGANOMETALLIC COMPOUND; PIPERIDINE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS; CHEMISTRY; CONFORMATION; SYNTHESIS;

AZO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOHEPTANES; HETEROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PIPERIDINES; THIOSEMICARBAZONES;

EID: 84902665556     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503309u     Document Type: Article

References (68)

1. Hou, X.-L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J., Eds.; Pergamon: Oxford, 2008; Vol. 19.
2. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635
3. Yet, L. Chem. Rev. 2000, 100, 2963
4. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813
5. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
6. Zhao, W. Chem. Rev. 2010, 110, 1706
7. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990; pp 1-208.
8. The Alkaloids, Bindra, J. S.; Manske, R. H. F., Eds.; Academic Press: New York, 1973; Vol. 14.
9. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
10. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49
11. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791
12. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
13. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863
14. Broggini, G.; Zecchi, G. Synthesis 1999, 905
15. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; Wiley: New York, 2003.
16. Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2005, 44, 6272
17. álvarez-Corral, M.; Muñoz-Dorado, M.; Rodríguez- García, I. Chem. Rev. 2008, 108, 3174
18. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887
19. Engels, B.; Christl, M. Angew. Chem., Int. Ed. 2009, 48, 7968
20. Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784
21. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156
22. Chen, Q.-A.; Wang, D.-S.; Zhou, Y.-G. Chem. Commun. 2010, 46, 4043
23. Narayan, R.; Potowski, M.; Jia, Z.-J.; Antonchick, A. P.; Waldmann, H. Acc. Chem. Res. 2014, 47, 1296
24. Huang, J.-Z.; Luo, S.-W.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 879
25. Tong, M.-C.; Chen, X.; Tao, H.-Y.; Wang, C.-J. Angew. Chem., Int. Ed. 2013, 52, 12377
26. Potowski, M.; Schürmann, M.; Preut, H.; Antonchick, A. P.; Waldmann, H. Nat. Chem. Biol. 2012, 8, 428
27. He, L.; Chen, X.-H.; Wang, D.-N.; Luo, S.-W.; Zhang, W.-Q.; Yu, J.; Ren, L.; Gong, L.-Z. J. Am. Chem. Soc. 2011, 133, 13504
28. Kim, H. Y.; Li, J.-Y.; Kim, S.; Oh, K. J. Am. Chem. Soc. 2011, 133, 20750
29. Chen, X.-H.; Zhang, W.-Q.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 5652
30. Zeng, W.; Chen, G.-Y.; Zhou, Y.-G.; Li, Y.-X. J. Am. Chem. Soc. 2007, 129, 750
31. Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuli, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338
32. Arai, T.; Yokoyama, N.; Mishiro, A.; Sato, H. Angew. Chem., Int. Ed. 2010, 49, 7895
33. Antonchick, A. P.; Gerding-Reimers, C.; Catarinella, M.; Schürmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735
34. Nájera, C.; Retamosa, M. D. G.; Sansano, J. Angew. Chem., Int. Ed. 2008, 47, 6055
35. Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174
36. Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2006, 45, 1979
37. Knoepfel, T. F.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971
38. Cabrera, S.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 16394
39. Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364
40. Yamashita, Y.; Imaizumi, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2011, 50, 4893
41. Potowski, M.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2012, 51, 9512
42. He, Z.-L.; Teng, H.-L.; Wang, C.-J. Angew. Chem., Int. Ed. 2013, 52, 2934
43. Teng, H.-L.; Yao, L.; Wang, C.-J. J. Am. Chem. Soc. 2014, 136, 4075
44. Liu, H.; Wu, Y.; Zhao, Y.; Li, Z.; Zhang, L.; Yang, W.; Jiang, H.; Jing, C.; Yu, H.; Wang, B.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2014, 136, 2625
45. Nakajima, T.; Katagiri, S. Bull. Chem. Soc. Jpn. 1962, 35, 910
46. Griffiths, J.; Lockwood, M. J. Chem. Soc., Perkin Trans. 1 1976, 1, 48
47. Dewar, M. J. S. Nature (London) 1945, 155, 50
48. Dewar, M. J. S. Nature (London) 1945, 155, 141
49. Wang, C.-J.; Liang, G.; Xue, Z.-Y.; Gao, F. J. Am. Chem. Soc. 2008, 130, 17250
50. Yan, D.-C.; Li, Q.-H.; Wang, C.-J. Chin. J. Chem. 2012, 30, 2714
51. Liu, T.-L.; He, Z.-L.; Tao, H.-Y.; Cai, Y.-P.; Wang, C.-J. Chem. Commun. 2011, 47, 2616
52. Wang, M.; Wang, C.-J.; Lin, Z. Organometallic 2012, 31, 7870
53. Tong, M.-C.; Li, J.; Tao, H.-Y.; Li, Y.-X.; Wang, C.-J. Chem.-Eur. J. 2011, 17, 12922
54. Xue, Z.-Y.; Li, Q.-H.; Tao, H.-Y.; Wang, C.-J. J. Am. Chem. Soc. 2011, 133, 11757
55. Kobayashi, J. i.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901
56. Mu, S.-Z.; Wang, J.-S.; Yang, X.-S.; He, H.-P.; Li, C.-S.; Di, Y.-T.; Wang, Y.; Zhang, Y.; Fang, X.; Huang, L.-J.; Hao, X.-J. J. Nat. Prod. 2008, 71, 564
57. Zhang, C.-R.; Liu, H.-B.; Feng, T.; Zhu, J.-Y.; Geng, M.-Y.; Yue, J.-M. J. Nat. Prod. 2009, 72, 1669
58. Zhang, C.-R.; Fan, C.-Q.; Dong, S.-H.; Liu, H.-B.; Zhou, W.-B.; Wu, Y.; Yue, J.-M. Org. Lett. 2011, 13, 2440
59. Luo, D.-Q.; Zhu, W.-L.; Yang, X.-L.; Liang, S.-J.; Cao, Z.-R. Helv. Chim. Acta 2010, 93, 1209
60. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds. Wiley-VCH: Weinheim, 2005.
61. Trost, B. M.; Jiang, C. Synthesis 2006, 369
62. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A 2004, 101, 5363
63. Mahendar, V.; Oikawa, H.; Oguri, H. Chem. Commun. 2013, 49, 2299
64. Blair, J. A.; Tate, C. J. J. Chem. Soc. (C) 1971, 1592
65. Blair, J. A.; Tate, C. J. J. Chem. Soc. Chem. Commun. 1970, 1319
66. Oda, M.; Kainuma, H.; Uchiyama, T.; Miyatake, R.; Kuroda, S. Tetrahedron 2003, 59, 2831
67. Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucher, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006
68. Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1981, 46, 4327