Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon–carbon bond cleavage

Chemical Communications

Volumn 47, Issue 17, 2011, Pages 5049-5051

  Li, Lei ^a   Wu, Xingxing ^a   Zhang, Junliang ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; ISOMERASE; LEWIS ACID; N TOSYLAZIRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION OPTIMIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79954430387     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc10926j     Document Type: Article

References (82)

1. C. Nájera, J. M. Sansano, Angew. Chem., Int. Ed. 2005, 44, 6272
2. Y. Cheng, Z.-T. Huang, M.-X. Wang, Curr. Org. Chem. 2004, 8, 325
3. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
4. F.-X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712
5. W. H. Pearson, P. Stoy, Synlett 2003, 903
6. W. H. Pearson, Pure Appl. Chem. 2002, 74, 1339
7. Pharmaceuticals, ed. J. L. McGuire, Wiley-VCH, Weinheim, vol. 1-4, 2000
8. C. Nájera, J. M. Sansano, Top. Heterocycl. Chem, 12, 117
9. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484
10. I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765
11. C. Nájera, J. M. Sansano, Angew. Chem., Int. Ed. 2005, 44, 6272
12. C. Nájera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105
13. Synthetic Applications of 1,3-Dipolar Cyclo-addition Chemistry Towards Heterocycles and Natural Products, ed. A. Padwa and W. H. Pearson, Wiley, New York, 2003
14. S. Kanemasa, Synlett 2002, 1371
15. K. V. Gothelf, in Cycloaddition Reactions in Organic Synthesis, ed. S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, 2002, p. 211
16. T. Arai, A. Mishiro, N. Yokoyama, K. Suzuki, H. Sato, J. Am. Chem. Soc. 2010, 132, 5338
17. T. Arai, N. Yokoyama, A. Mishiro, H. Sato, Angew. Chem., Int. Ed. 2010, 49, 7895
18. J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247
19. V. H. Dahanukar, L. A. Zavialov, Curr. Opin. Drug Discovery Dev. 2002, 5, 918
20. X. E. Hu, Tetrahedron 2004, 60, 2701
21. L. G. Ma, J. X. Xu, Prog. Chem. 2004, 16, 220
22. I. D. G. Watson, L. Yu, A. K. Yudin, Acc. Chem. Res. 2006, 39, 194
23. A. Padwa, in Comprehensive Heterocyclic Chemistry III, ed. A. R. Katrizky, C. A. Ramsden, E. F. V. Scriven and R. J. K. Taylor, Elsevier, Amsterdam, 2008, vol. 1, p. 2
24. M. D'hooghe, V. Van Speybroeck, M. Waroquier, N. De Kimpe, Chem. Commun. 2006, 1554
25. C.-H. Ding, L.-X. Dai, X.-L. Hou, Synlett 2004, 1691
26. R. J. Madhushaw, C.-C. Hu, R.-S. Liu, Org. Lett. 2002, 4, 4151
27. I. Prathap, P. S. Srihari, K. Pandey, B. V. S. Reddy, J. S. Yadav, Tetrahedron Lett. 2001, 42, 9089
28. M. Nakagawa, M. Kawahara, Org. Lett. 2000, 2, 953
29. I. Unhureanu, P. Klotz, A. Mann, Angew. Chem., Int. Ed. 2000, 39, 4615
30. C. Gaebert, J. Mattay, Tetrahedron 1997, 53, 14297
31. P. A. Wender, D. Strand, J. Am. Chem. Soc. 2009, 131, 7528
32. B. Kang, W. A. Miller, S. Goyal, S. T. Nguyen, Chem. Commun. 2009, 3928
33. S. Gandhi, A. Bisai, B. A. B. Prasad, V. K. Singh, J. Org. Chem. 2007, 72, 2133
34. M. K. Ghorai, K. Ghosh, Tetrahedron Lett. 2007, 48, 3191
35. V. K. Yadav, V. Sriramurthy, J. Am. Chem. Soc. 2005, 127, 16366
36. A. Sudo, Y. Morioko, E. Koizumi, F. Sanda, T. Endo, Tetrahedron Lett. 2003, 44, 7889
37. J. O. Baeg, C. Bensimon, H. Alper, J. Am. Chem. Soc. 1995, 117, 4700
38. J. O. Baeg, H. Alper, J. Org. Chem. 1992, 57, 157
39. H. Maas, C. Bensimon, H. Alper, J. Org. Chem. 1998, 63, 17
40. T. Munegumi, I. Azumaya, T. Kato, H. Masu, S. Saito, Org. Lett. 2006, 8, 379
41. X. Sun, W. Sun, R. Fan, J. Wu, Adv. Synth. Catal. 2007, 349, 2151
42. M. Bera, S. J. Roy, J. Org. Chem. 2009, 74, 8814
43. D. Hong, X. Lin, Y. Zhu, Y. Wang, Org. Lett. 2009, 11, 5678
44. Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6312
45. I. Fujimori, T. Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 16438
46. E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 12084
47. K. Arai, S. Lucarini, M. M. Salter, K. Ohta, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2007, 129, 8103
48. B. Wu, J. C. Gallucci, J. R. Parquette, T. V. RajanBabu, Angew. Chem., Int. Ed. 2009, 48, 1126
49. B. Wu, J. R. Parquette, T. V. RajanBabu, Science 2009, 326, 1662
50. H. W. Heine, R. Peavy, Tetrahedron Lett. 1965, 6, 3123
51. A. Padwa, L. Hamilton, Tetrahedron Lett. 1965, 6, 4363
52. R. Huisgen, W. Scheer, G. Szeimies, H. Huber, Tetrahedron Lett. 1966, 7, 397
53. R. Huisgen, W. Scheer, H. Huber, J. Am. Chem. Soc. 1967, 89, 1753-1755
54. R. Huisgen, W. Scheer, H. Mäder, Angew. Chem., Int. Ed. Engl. 1969, 8, 602
55. M. Vaultier, R. Carrie, Tetrahedron Lett. 1978, 19, 1195
56. P. D. Pohlhaus, R. K. Bowman, J. S. Johnson, J. Am. Chem. Soc. 2004, 126, 2294-2295
57. T. Wang, J. Zhang, Chem.-Eur. J. 2011, 17, 86
58. Z. Chen, L. Wei, J. Zhang, Org. Lett. 2011, 13, 1170
59. R. H. Crabtree, Chem. Rev. 1985, 85, 245
60. P. W. Jennings, L. L. Johnson, Chem. Rev. 1994, 94, 2241
61. M. Murakami, and Y. Ito, in Activation of Unreactive Bonds and Organic Synthesis, ed. S. Murai, Springer, New York, 1999, vol. 3, p. 97
62. B. Rybtchinski, D. Milstein, Angew. Chem., Int. Ed. 1999, 38, 870
63. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759
64. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610
65. W. D. Jones, Nature 1993, 364, 676
66. R. Fan, Y. Ye, Adv. Synth. Catal. 2008, 350, 1526
67. R. Fan, L. Wang, Y. Ye, J. Zhang, Tetrahedron Lett. 2009, 50, 3857
68. G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126, 9544
69. J.-X. Ji, J. Wu, A. S. C. Chan, Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 11196
70. D. A. Evans, J. Wu, J. Am. Chem. Soc. 2005, 127, 8006
71. D. A. Evans, K. R. Fandrick, H. J. Song, J. Am. Chem. Soc. 2005, 127, 8942
72. S. W. Smith, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 12645
73. J.-F. Zhao, H.-Y. Tsui, P.-J. Wu, J. Lu, T.-P. Loh, J. Am. Chem. Soc. 2008, 130, 16492
74. Y.-J. Zhao, B. Li, L.-J. S. Tan, Z.-L. Shen, T.-P. Loh, J. Am. Chem. Soc. 2010, 132, 10242
75. J.-F. Zhao, B.-H. Tan, T.-P. Loh, Chem. Sci. 2011, 2, 345
76. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151
77. M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321
78. Y. Xiao, and J. Zhang, in Handbook of Cyclization Reactions, ed. S. Ma, Wiley-VCH, Weinheim, 2010, vol. 2, p. 733
79. I. S. Young, M. A. Kerr, Angew. Chem., Int. Ed. 2003, 42, 3023
80. M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc. 2005, 127, 5764
81. Y.-B. Kang, X.-L. Sun, Y. Tang, Angew. Chem., Int. Ed. 2007, 46, 3918
82. Y. Zhang, F. Liu, J. Zhang, Chem.-Eur. J. 2010, 16, 6146