Enantio- and diastereoselective synthesis of spiro-epoxyoxindoles

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 3924-3929

  Boucherif, Amina ^a   Yang, Qing Qing ^a   Wang, Qiang ^a   Chen, Jia Rong ^a   Lu, Liang Qiu ^a   Xiao, Wen Jing ^a,b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b SynBio Research Platform   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

ASYMMETRIC SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVITIES; ENANTIO; HIGH YIELD; MILD REACTION CONDITIONS; SULFONIUM SALTS; SULFUR YLIDES;

STEREOSELECTIVITY;

CAMPHOR; ISATIN; OXINDOLE; SPIRO COMPOUND; SPIROEPOXYOXINDOLE DERIVATIVE; SULFONIUM DERIVATIVE; SULFUR; UNCLASSIFIED DRUG; EPOXIDE; INDOLE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL MODEL; CHIRALITY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EPOXY COMPOUNDS; INDOLES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84899822619     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5003856     Document Type: Article

References (54)

1. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
2. Trost, B.; Brennan, M. Synthesis 2009, 3003
3. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
4. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
5. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 335, 1023
6. Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863
7. Dandia, A.; Singh, R.; Bhaskaran, S. Ultrason. Sonochem. 2010, 17, 399
8. Chouhan, M.; Senwar, K. R.; Sharma, R.; Grover, V.; Nair, V. A. Green Chem. 2011, 13, 2553
9. Wang, L.; Li, Z.; Lu, L.; Zhang, W. Tetrahedron 2012, 68, 1483
10. Wang, L.; Su, Y.; Xu, X.; Zhang, W. Eur. J. Org. Chem. 2012, 6606
11. Brunton, S. A.; Jones, K. J. Chem. Soc., Perkin Trans. 1 2000, 763
12. Dandia, A.; Singh, R.; Saha, M.; Shivpuri, A. Pharmazie 2002, 57, 602
13. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
14. Marx, K. A.; O'Neil, P.; Hoffman, P.; Ujwal, M. L. J. Chem. Inf. Comput. Sci. 2003, 43, 1652
15. Dandia, A.; Singh, R.; Bhaskaran, S. Ultrason. Sonochem. 2011, 18, 1113
16. Gasperi, T.; Loreto, M. A.; Migliorini, A.; Ventura, C. Eur. J. Org. Chem. 2011, 385
17. Palumbo, C.; Mazzeo, G.; Mazziotta, A.; Gambacorta, A.; Loreto, M. A.; Migliorini, A.; Superchi, S.; Tofani, D.; Gasperi, T. Org. Lett. 2011, 13, 6248 and references cited therein
18. Muthusamy, S.; Gunanathan, C.; Nethaji, M. Synlett 2004, 639
19. Muthusamy, S.; Karikalan, T.; Suresh, E. Tetrahedron Lett. 2011, 52, 1934
20. Baiocchi, L.; Giannangili, M. J. Heterocycl. Chem. 1988, 25, 1905
21. Shmidt, M. S.; Reverdito, A. M.; Kremenchuzky, L.; Perillo, I. A.; Blanco, M. M. Molecules 2008, 13, 831
22. Shmidt, M. S.; Perillo, I. A.; González, M.; Blanco, M. M. Tetrahedron Lett. 2012, 53, 2514
23. Fu, Q.; Yan, C. G. Beilstein J. Org. Chem. 2013, 9, 918
24. Bravo, P.; Gaudiano, G.; Umani-Ronchi, A. Tetrahedron Lett. 1969, 9, 679
25. Schulz, V.; Davoust, M.; Lemarie, M.; Lohier, J. F.; Santos, J. S.; Metzner, P.; Briere, J. F. Org. Lett. 2007, 9, 1745
26. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241
27. Sun, X.; Tang, Y. Acc. Chem. Res. 2008, 41, 937
28. Luo, Y.-C; Zhang, H.-H.; Wang, Y.; Xu, P.-F. Acc. Chem. Res. 2010, 43, 1317
29. Arrayás, R. G.; Carretero, J. C. Chem. Commun. 2011, 47, 2207
30. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341
31. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611
32. McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841 and ref 7b
33. Goodridge, R.; Hambley, T. W.; Haynes, R. K.; Ridley, D. D. J. Org. Chem. 1988, 53, 2881
34. Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489
35. Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. J. Chem. Soc., Perkin Trans. 1 1999, 77
36. Aggarwal, V. K.; Hynd, G.; Picoul, W.; Vasse, J. J. Am. Chem. Soc. 2002, 124, 9964
37. Fujiki, K.; Tanifuji, N.; Sasaki, Y.; Yokoyama, T. Synthesis 2002, 343
38. Aggarwal, V. K.; Fang, G. Y.; Schmidt, A. T. J. Am. Chem. Soc. 2005, 127, 1642
39. Aggarwal, V. K.; Charmant, J. P. H.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.; Winn, C. L. J. Am. Chem. Soc. 2006, 128, 2105
40. Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730
41. Fang, G. Y.; Wallner, O. A.; Blasio, N. D.; Ginesta, X.; Harvey, J. N.; Aggarwal, V. K. J. Am. Chem. Soc. 2007, 129, 14632
42. Zheng, J.-C.; Zhu, C.-Y.; Sun, X.-L.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2008, 73, 6909
43. Wang, Q.-G.; Deng, X.-M.; Zhu, B.-H.; Ye, L.-W.; Sun, X.-L.; Li, C.-Y.; Zhu, C.-Y.; Shen, Q.; Tang, Y. J. Am. Chem. Soc. 2008, 130, 5408
44. Zhu, B.-H.; Zhou, R.; Zheng, J.-C.; Deng, X.-M.; Sun, X.-L.; Shen, Q.; Tang, Y. J. Org. Chem. 2010, 75, 3454
45. Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278
46. Lu, L.-Q.; Ming, Z.-H.; An, J.; Li, C.; Chen, J.-R.; Xiao, W.-J. J. Org. Chem. 2012, 77, 1072
47. Lu, L.-Q.; Li, F.; An, J.; Cheng, Y.; Chen, J.-R.; Xiao, W.-J. Chem.-Eur. J. 2012, 18, 4073
48. Yang, Q.-Q.; Xiao, C.; Lu, L.-Q.; An, J.; Tan, F.; Li, B.-J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 9137
49. An, J.; Lu, L.-Q.; Yang, Q.-Q.; Wang, T.; Xiao, W.-J. Org. Lett. 2013, 15, 542
50. Cheng, Y.; Hu, X.-Q.; Gao, S.; Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Tetrahedron 2013, 69, 3810
51. Yang, Q.-Q; Wang, Q.; An, J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Chem.-Eur. J. 2013, 19, 8401
52. Dandia, A.; Singh, R.; Saha, M.; Shivpuri, A. Pharmazie 2002, 57, 602 and references therein
53. Yang, Q.; Xiao, W.-J.; Yu, Z.-K. Org. Lett. 2005, 7, 871
54. Trost, B.-M.; Zhang, Y. J. Am. Chem. Soc. 2007, 129, 14548