Highly chemoselective rauhut-currier reaction between maleimides and enones and dual phosphine-mediated one-pot synthesis of bicyclic and polycyclic skeletons

Journal of Organic Chemistry

Volumn 78, Issue 21, 2013, Pages 10596-10604

  Zhou, Rong ^a   Wang, Jianfang ^a   Yu, Jia ^a   He, Zhengjie ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE; CROSS-COUPLING PRODUCTS; INTRAMOLECULAR WITTIG REACTION; MALEIMIDES; ONE-POT SYNTHESIS; POLYCYCLIC COMPOUNDS; TANDEM SEQUENCE;

MUSCULOSKELETAL SYSTEM;

PHOSPHORUS COMPOUNDS;

CHEMICAL COMPOUND; ENONE; MALEIMIDE DERIVATIVE; PHOSPHINE; POLYCYCLIC HYDROCARBON; PYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; RAUHUT CURRIER REACTION; WITTIG REACTION;

EID: 84887095592     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401363u     Document Type: Article

References (79)

1. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138
2. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726
3. Rauhut, M.; Currier, H. (American Cyanamid Co.), U.S. Patent 3,074,999, 1963
4. Chem. Abstr. 1963, 58, 11224a.
5. Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069
6. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
7. Erguden, J. K.; Moore, H. W. Org. Lett. 1999, 1, 375
8. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404
9. Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402
10. Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737
11. Mergott, D. J.; Frank, S. A.; Roush, W. R. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11955
12. Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223
13. Stark, L. M.; Pekari, K.; Sorensen, E. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 12064
14. Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379
15. Aroyan, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 256
16. Seidel, F.; Gladysz, J. A. Synlett 2007, 986
17. Marqués-López, E.; Herrera, R. P.; Marks, T.; Jacobs, W. C.; Könning, D.; de Figueiredo, R. M.; Christmann, M. Org. Lett. 2009, 11, 4116
18. Gong, J.-J.; Li, T.-Z.; Pan, K.; Wu, X.-Y. Chem. Commun. 2011, 47, 1491
19. Takizawa, S.; Nguyen, T. M.-N.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423
20. Wang, X.-F.; Peng, L.; An, J.; Li, C.; Yang, Q.-Q.; Liu, L.-Q.; Gu, F.-L.; Xiao, W.-J. Chem.-Eur. J. 2011, 17, 6484
21. Dermenci, A.; Selig, P. S.; Domaoal, R. A.; Spasov, K. A.; Anderson, K. S.; Miller, S. J. Chem. Sci. 2011, 2, 1568
22. Evans, C. A.; Miller, S. J. J. Am. Chem. Soc. 2003, 125, 12394
23. Sun, X.; Sengupta, S.; Petersen, J. L.; Wang, H.; Lewis, J. P.; Shi, X. Org. Lett. 2007, 9, 4495
24. Zhong, C.; Chen, Y.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. Angew. Chem., Int. Ed. 2009, 48, 1279
25. Zhao, Q.-Y.; Pei, C.-K.; Guan, X.-Y.; Shi, M. Adv. Synth. Catal. 2011, 353, 1973
26. Wang, J.; Xie, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177
27. Reynolds, T. E.; Binkley, M. S.; Scheidt, K. A. Org. Lett. 2008, 10, 2449
28. Dadwal, M.; Mohan, R.; Panda, D.; Mobin, S. M.; Namboothiri, I. N. N. Chem. Commun. 2006, 338
29. Shanbhag, P.; Nareddy, P. R.; Dadwal, M.; Mobin, S. M.; Namboothiri, I. N. N. Org. Biomol. Chem. 2010, 8, 4867
30. Lee, C. H.; Lee, K.-J. Synthesis 2004, 1941
31. Morita, K.; Kobayashi, T. Bull. Chem. Soc. Jpn. 1969, 42, 2732
32. McClure, J. D. J. Org. Chem. 1970, 35, 3045
33. Baizer, M. M.; Anderson, J. D. J. Org. Chem. 1965, 30, 1357
34. Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989, 30, 7381
35. Hall, C. D.; Lowther, N.; Tweedy, B. R.; Hall, A. C.; Shaw, G. J. Chem. Soc., Perkin Trans. 2 1998, 2047
36. Jenner, G. Tetrahedron Lett. 2000, 41, 3091
37. Su, W.; Mcleod, D.; Verkade, J. G. J. Org. Chem. 2003, 68, 9499
38. McDougal, S. E.; Schaus, S. E. Angew. Chem., Int. Ed. 2006, 45, 3117
39. Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477
40. Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. Stud. Nat. Prod. Chem. 2003, 29, 449
41. Wu, H.; Zhang, H.; Zhao, G. Tetrahedron 2007, 63, 6454
42. Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467
43. Silva, L. F. Tetrahedron 2002, 58, 9137
44. Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906
45. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535
46. Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937
47. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
48. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
49. Xu, S.; He, Z. RSC Adv. 2013, 3, 16885
50. Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118
51. Kao, T.-T.; Syu, S.-E.; Jhang, Y.-W.; Lin, W. Org. Lett. 2010, 12, 3066
52. Lee, C.-J.; Jang, Y.-J.; Wu, Z.-Z.; Lin, W. Org. Lett. 2012, 14, 1906
53. Wang, J.; Zhou, R.; He, Z.-R.; He, Z. Eur. J. Org. Chem. 2012, 6033
54. Lee, Y.-T.; Jang, Y.-J.; Syu, S.-E.; Chou, S.-C.; Lee, C.-J.; Lin, W. Chem. Commun. 2012, 48, 8135
55. Lu, Y.; Arndtsen, B. A. Org. Lett. 2009, 11, 1369
56. Morin, M. S. T.; Aly, S.; Arndtsen, B. A. Chem. Commun. 2013, 49, 883
57. Yavari, I.; Bayat, M. J. Synlett 2010, 2293
58. Tian, J.; He, Z. Chem. Commun. 2013, 49, 2058
59. Zhou, R.; Wang, J.; Duan, C.; He, Z. Org. Lett. 2012, 14, 6134
60. Xu, S.; He, Z. Chin. J. Org. Chem. 2012, 32, 1159
61. Hedaya, E.; Theodoropulos, S. Tetrahedron 1968, 24, 2241
62. Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470
63. Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem.-Eur. J. 2009, 15, 8698
64. Cai, L.; Zhang, B.; Wu, G.; Song, H.; He, Z. Chem. Commun. 2011, 47, 1045
65. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863
66. Zhao, Q.; Han, X.; Wei, Y.; Shi, M.; Lu, Y. Chem. Commun. 2012, 48, 970
67. Znabet, A.; Polak, M. M.; Janssen, E.; de Kanter, F. J. J.; Turner, N. J.; Orru, R. V. A.; Ruijter, E. Chem. Commun. 2010, 46, 7918
68. Kohler, V.; Bailey, K. R.; Znabet, A.; Raftery, J.; Helliwell, M.; Turner, N. J. Angew. Chem., Int. Ed. 2010, 49, 2182
69. Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
70. Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037
71. Westermann, B.; Ayaz, M.; van Berkel, S. S. Angew. Chem., Int. Ed. 2010, 49, 846
72. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
73. Yao, W.; Wu, Y.; Wang, G.; Zhang, Y.; Ma, C. Angew. Chem., Int. Ed. 2009, 48, 9713
74. Ma, J.; Xie, P.; Hu, C.; Huang, Y.; Chen, R. Chem.-Eur. J. 2011, 17, 7418
75. Xie, P.; Huang, Y.; Lai, W.; Meng, X.; Chen, R. Org. Biomol. Chem. 2011, 9, 6707
76. Shi, Z.; Tong, Q.; Leong, W. W. Y.; Zhong, G. Chem.-Eur. J. 2012, 18, 9802
77. Shi, Z.; Yu, P.; Loh, T.-P.; Zhong, G. Angew. Chem., Int. Ed. 2012, 51, 7825
78. Sortino, M.; Garibotto, F.; Cechinel Filho, V.; Gupta, M.; Enriz, R.; Zacchino, S. Bioorg. Med. Chem. 2011, 19, 2823
79. Lawerence, N. J.; Crump, J. P.; McGown, A. T.; Hadfield, J. A. Tetrahedron Lett. 2001, 42, 3939