One-Pot Tandem Diastereoselective and Enantioselective Synthesis of Functionalized Oxindole-Fused Spiropyrazolidine Frameworks

Chemistry - A European Journal

Volumn 20, Issue 41, 2014, Pages 13136-13142

  Mei, Liang Yong ^a   Tang, Xiang Ying ^a,b   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

ligands; oxindoles; palladium; pyrazolidines; tandem reactions

Indexed keywords

ENANTIOSELECTIVITY; LIGANDS; PALLADIUM;

ASYMMETRIC [3+2] CYCLOADDITION; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; OXINDOLES; PYRAZOLIDINES; STEREOGENIC CENTERS; TANDEM REACTION;

STEREOSELECTIVITY;

EID: 84941065859     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403990     Document Type: Article

References (113)

1. J. Yang, X. Z. Wearing, P. W. LeQuesne, J. R. Deschamps, J. M. Cook, J. Nat. Prod. 2008, 71, 1431-1440;
2. P. R. Sebahar, R. M. Williams, J. Am. Chem. Soc. 2000, 122, 5666-5667;
3. T. Onishi, P. R. Sebahar, R. M. Williams, Org. Lett. 2003, 5, 3135-3137;
4. S. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino, N. Rosen, J. Am. Chem. Soc. 1999, 121, 2147-2155;
5. T. D. Bagul, G. Lakshmaiah, T. Kawabata, K. Fuji, Org. Lett. 2002, 4, 249-251;
6. K. A. Miller, S. Tsukamoto, R. M. Williams, Nat. Chem. 2009, 1, 63-68;
7. B. M. Trost, N. Cramer, H. Bernsmann, J. Am. Chem. Soc. 2007, 129, 3086-3087;
8. K. Ding, Y. Lu, Z. Nikolovska-Coleska, G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey, K. Krajewski, P. P. Roller, S. Wang, J. Med. Chem. 2006, 49, 3432-3435;
9. C.-B. Cui, H. Kakeya, H. J. Osada, Tetrahedron 1996, 52, 12651-12666;
10. T. J. Greshock, A. W. Grubbs, P. Jiao, D. T. Wicklow, J. B. Gloer, R. M. Williams, Angew. Chem. 2008, 120, 3629-3633;
11. Angew. Chem. Int. Ed. 2008, 47, 3573-3577;
12. G. Laus, D. Brossner, K. Keplinger, Phytochemistry 1997, 45, 855-860;
13. A. Thangamani, Eur. J. Med. Chem. 2010, 45, 6120-6126.
14. For recent reviews, see:
15. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104-6155;
16. K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci. 2012, 3, 327-334;
17. R. Rios, Chem. Soc. Rev. 2012, 41, 1060-1074;
18. R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 2012, 41, 7247-7290;
19. N. R. Ball-Jones, J. J. Badillo, A. K. Franz, Org. Biomol. Chem. 2012, 10, 5165-5181;
20. J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156-1171;
21. J. J. Badillo, N. V. Hanhan, A. K. Franz, Curr. Opin. Drug Di. Dev. 2010, 13, 758-776;
22. F. Zhou, Y. L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381-1407;
23. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003-3025;
24. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902-8912;
25. Angew. Chem. Int. Ed. 2007, 46, 8748-8758;
26. H. Lin, S. J. Danishefsky, Angew. Chem. 2003, 115, 38-53;
27. Angew. Chem. Int. Ed. 2003, 42, 36-51;
28. R. M. Williams, R. J. Cox, Acc. Chem. Res. 2003, 36, 127-139;
29. A. B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945-2963;
30. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209-2219.
31. S. Muthusamy, D. Azhagan, B. Gnanaprakasam, E. Suresh, Tetrahedron Lett. 2010, 51, 5662-5665;
32. B. V. S. Reddy, T. Rajasekaran, G. Karthik, T. P. Rao, Tetrahedron Lett. 2012, 53, 3416-3420;
33. C. Meyers, E. M. Carreira, Angew. Chem. 2003, 115, 718-720;
34. Angew. Chem. Int. Ed. 2003, 42, 694-696;
35. D. D. Schwarzer, P. J. Gritsch, T. Gaich, Angew. Chem. 2012, 124, 11682-11684;
36. Angew. Chem. Int. Ed. 2012, 51, 11514-11516;
37. C. Marti, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 11505-11515;
38. Z.-Y. Cao, X. Wang, C. Tan, X.-L. Zhao, J. Zhou, K. Ding, J. Am. Chem. Soc. 2013, 135, 8197-8200;
39. Z.-Y. Cao, F. Zhou, Y.-H. Yu, J. Zhou, Org. Lett. 2012, 15, 42-45;
40. S. A. Bonderoff, A. Padwa, Org. Lett. 2013, 15, 4114-4117;
41. S. Muthusamy, C. Gunanathan, M. Nethaji, Synlett 2004, 639-642.
42. S. Muthusamy, C. Gunanathan, S. A. Babu, E. Suresh, P. Dastidar, Chem. Commun. 2002, 824-825;
43. S. Muthusamy, T. Karikalan, C. Gunanathan, E. Suresh, Tetrahedron 2012, 68, 1595-1605;
44. S. Muthusamy, P. Srinivasan, Tetrahedron Lett. 2009, 50, 3794-3797;
45. B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc. 2011, 133, 20611-20622;
46. S. Muthusamy, C. Gunanathan, Synlett 2003, 1783-1786.
47. S. Muthusamy, R. Ramkamar, A. K. Mishra, Tetrahedron Lett. 2011, 52, 148-150;
48. B. Alcaide, P. Almendros, C. Aragoncillo, R. Callejo, M. P. Ruiz, M. R. Torres, Eur. J. Org. Chem. 2012, 2359-2366;
49. L. Ren, X.-L. Lian, L.-Z. Gong, Chem. Eur. J. 2013, 19, 3315-3318;
50. X. Guo, W.-H. Hu, Acc. Chem. Res. 2013, 46, 2427-2440;
51. S. Muthusamy, C. Gunanathan, M. Nethaji, J. Org. Chem. 2004, 69, 5631-5637;
52. D. Xing, C.-C. Jing, X.-F. Li, H. Qiu, W.-H. Hu, Org. Lett. 2013, 15, 3578-3581.
53. S. Muthusamy, D. Azhagan, Tetrahedron Lett. 2011, 52, 6732-6735;
54. S. Muthusamy, K. Selvaraj, Tetrahedron Lett. 2013, 54, 6886-6888;
55. Y. Qian, C.-C. Jing, C.-W. Zhai, W.-H. Hu, Adv. Synth. Catal. 2012, 354, 301-307.
56. R. Augusti, C. Kascheres, J. Org. Chem. 1993, 58, 7079-7083.
57. S. Kanemasa, T. Kanai, J. Am. Chem. Soc. 2000, 122, 10710-10711.
58. M. D. Carriõn, M. E. Camacho, J. Leon, G. Escames, V. Tapias, D. A. Castroviejo, M. A. Gallo, A. Espinosa, Tetrahedron 2004, 60, 4051-4069;
59. R. Muruganantham, S. M. Mobin, I. N. N. Namboothiri, Org. Lett. 2007, 9, 1125-1128.
60. T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2174-2175;
61. M. P. Sibi, L. M. Stanley, T. Soeta, Org. Lett. 2007, 9, 1553-1556;
62. H. Suga, Y. Furihata, A. Sakamoto, K. Itoh, Y. Okumura, T. Tsuchida, A. Kakehi, T. Baba, J. Org. Chem. 2011, 76, 7377-7387;
63. S. He, L. Chen, Y.-N. Niu, L.-Y. Wu, Y.-M. Liang, Tetrahedron Lett. 2009, 50, 2443-2445;
64. X. Qi, J. M. Ready, Angew. Chem. 2007, 119, 3306-3308;
65. Angew. Chem. Int. Ed. 2007, 46, 3242-3244.
66. M. Kissane, S. E. Lawrence, A. R. Maguire, Org. Biomol. Chem. 2010, 8, 2735-2748;
67. Y. Hari, S. Tsuchida, R. Sone, T. Aoyama, Synthesis 2007, 21, 3371-3375;
68. J.-W. Xie, Z. Wang, W.-J. Yang, L.-C. Kong, D.-C. Xu, Org. Biomol. Chem. 2009, 7, 4352-4354;
69. T. Hanamoto, Y. Hakoshima, M. Egashira, Tetrahedron Lett. 2004, 45, 7573-7576.
70. Z. Goldschmidt, B. Crammer, Chem. Soc. Rev. 1988, 17, 229-267;
71. T. Hudlicky, T. M. Kutchan, S. M. Naqvi, Org. React. 1985, 33, 247-335;
72. K. Burgess, J. Org. Chem. 1987, 52, 2046-2051;
73. Y. Morizawa, K. Oshima, H. Nozaki, Tetrahedron Lett. 1982, 23, 2871-2874;
74. K. Hiroi, A. Yamada, Tetrahedron: Asymmetry 2000, 11, 1835-1841;
75. A. P. Dieskau, M. S. Holzwarth, B. Plietker, J. Am. Chem. Soc. 2012, 134, 5048-5051;
76. A. F. G. Goldberg, N. R. O'Connor, R. A. Craig II, B. M. Stoltz, Org. Lett. 2012, 14, 5314-5317;
77. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. White, S. C. Virgil, B. M. Stoltz, Nature Chem. 2012, 4, 130-133;
78. C. M. Reeves, C. Eidamshaus, J. Kim, B. M. Stoltz, Angew. Chem. 2013, 125, 6850-6853;
79. Angew. Chem. Int. Ed. 2013, 52, 6718-6721.
80. I. Shimizu, Y. Ohashi, J. Tsuji, Tetrahedron Lett. 1985, 26, 3825-3828;
81. I. Shimizu, Y. Ohashi, J. Tsuji, Chem. Lett. 1987, 6, 1157-1158;
82. A. T. Parsons, M. J. Campbell, J. S. Johnson, Org. Lett. 2008, 10, 2541-2544;
83. B. M. Trost, P. J. Morris, Angew. Chem. 2011, 123, 6291-6294;
84. Angew. Chem. Int. Ed. 2011, 50, 6167-6170;
85. A. F. G. Goldberg, B. M. Stoltz, Org. Lett. 2011, 13, 4474-4476;
86. L.-Y. Mei, Y. Wei, Q. Xu, M. Shi, Organometallics 2012, 31, 7591-7599;
87. L.-Y. Mei, Y. Wei, Q. Xu, M. Shi, Organometallics 2013, 32, 3544-3556.
88. R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 6330-6331;
89. N. D. Shapiro, Y. Shi, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 11654-11655;
90. X. Xu, Y. Qian, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2013, 135, 1244-1247;
91. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334-5335;
92. R. Na, C. Jing, Q. Xu, H. Jiang, X. Wu, J. Shi, J. Zhong, M. Wang, D. Benitez, E. Tkatchouk, W. A. Goddard III, H. Guo, O. Kwon, J. Am. Chem. Soc. 2011, 133, 13337-13348;
93. R. Shintani, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 10778-10779;
94. T. Imaizumi, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2012, 134, 20049-20052;
95. M. Wang, Z. Huang, J. Xu, Y. R. Chi, J. Am. Chem. Soc. 2014, 136, 1214-1217;
96. T. Hashimoto, M. Omote, K. Maruoka, Angew. Chem. 2011, 123, 3551-3554;
97. Angew. Chem. Int. Ed. 2011, 50, 3489-3492;
98. M.-C. Tong, X. Chen, H.-Y. Tao, C.-J. Wang, Angew. Chem. 2013, 125, 12603-12606;
99. Angew. Chem. Int. Ed. 2013, 52, 12377-12380;
100. H. Guo, H. Liu, F. Zhu, R. Na, H. Jiang, Y. Wu, L. Zhang, Z. Li, H. Yu, B. Wang, Y. Xiao, X.-P. Hu, M. Wang, Angew. Chem. 2013, 125, 12873-12877;
101. Angew. Chem. Int. Ed. 2013, 52, 12641-12645;
102. M. Keller, A. S. S. Sido, P. Pale, J. Sommer, Chem. Eur. J. 2009, 15, 2810-2817;
103. N. Luo, Z. Zheng, Z.-K. Yu, Org. Lett. 2011, 13, 3384-3387;
104. X. Fang, J. Li, H.-Y. Tao, C.-J. Wang, Org. Lett. 2013, 15, 5554-5557.
105. F. Khuong-Huu, M. Cesario, J. Guilhem, R. Goutarel, Tetrahedron 1976, 32, 2539-2543;
106. C. Kan, H.-P. Husson, H. Jacquemin, S.-K. Kan, M. Lounasmaa, Tetrahedron Lett. 1980, 21, 55-58;
107. C. Kan, H.-P. Husson, S.-K. Kan, M. Lounasmaa, Tetrahedron Lett. 1980, 21, 3363-3366;
108. M. E. Kuehne, T. H. Matsko, J. C. Bohnert, L. Motyka, D. O. Smith, J. Org. Chem. 1981, 46, 2002-2009;
109. W. G. Bornmann, M. E. Kuehne, J. Org. Chem. 1992, 57, 1752-1760;
110. M. E. Kuehne, U. K. Bandarage, A. Hammach, Y.-L. Li, T. Wang, J. Org. Chem. 1998, 63, 2172-2183;
111. I. P. Andrews, O. Kwon, Chem. Sci. 2012, 3, 2510-2514.
112. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881;
113. R. W. W. Hooft, L. H. Straver, A. L. Spek, J. Appl. Crystallogr. 2008, 41, 96-103.