Enantioselective assembly of spirocyclic oxindole-dihydropyranones through NHC-catalyzed cascade reaction of isatins with N -hydroxybenzotriazole esters of α,β-unsaturated carboxylic acid

Journal of Organic Chemistry

Volumn 80, Issue 6, 2015, Pages 3289-3294

  Que, Yonglei ^a   Li, Tuanjie ^a   Yu, Chenxia ^a   Wang, Xiang Shan ^a   Yao, Changsheng ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MATERIALS; CARBOXYLIC ACIDS; CATALYSIS; ESTERIFICATION; ESTERS; SYNTHESIS (CHEMICAL);

BIOLOGICAL SIGNIFICANCE; CASCADE REACTIONS; DIHYDROPYRANONES; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; HYDROXYBENZOTRIAZOLE; STEREOGENIC CENTERS; UNSATURATED CARBOXYLIC ACIDS;

ENANTIOSELECTIVITY;

BENZOTRIAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER; ISATIN DERIVATIVE; OXINDOLE; PYRAN DERIVATIVE; SPIRO COMPOUND; CARBENE; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; ISATIN; METHANE; PYRONE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; X RAY ANALYSIS; ANALOGS AND DERIVATIVES; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; ESTERS; HETEROCYCLIC COMPOUNDS; INDOLES; ISATIN; METHANE; MOLECULAR STRUCTURE; PYRONES; SPIRO COMPOUNDS; STEREOISOMERISM; TRIAZOLES;

EID: 84925357873     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502920w     Document Type: Article

References (50)

1. Endo, A. J. Med. Chem. 1985, 28, 401
2. Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567
3. Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147
4. Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666
5. Istvan, E. S.; Deisenhofer, J. Science 2001, 292, 1160
6. Bagul, T. D.; Lakshmaiah, G.; Kawabata, T.; Fuji, K. Org. Lett. 2002, 4, 249
7. Onishi, T.; Sebahar, P. R.; Williams, R. M. Org. Lett. 2003, 5, 3135
8. Shaw, S. J.; Sundermann, K. F.; Burlingame, M. A.; Myles, D. C.; Freeze, B. S.; Xian, M.; Brouard, I.; Smith, A. B., III J. Am. Chem. Soc. 2005, 127, 6532
9. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Shangary, S.; Gao, W.; Qin, D.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Wang, S. J. Med. Chem. 2006, 49, 3432
10. Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086
11. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
12. Yang, J.; Wearing, X. Z.; Le Quesne, P. W.; Deschamps, J. R.; Cook, J. M. J. Nat. Prod. 2008, 71, 1431
13. Miller, K. A.; Tsukamoto, S.; Williams, R. M. Nat. Chem. 2009, 1, 63
14. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
15. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
16. Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247
17. Lzquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
18. Ramachary, D. B.; Venkaiah, C.; Madhavachary, R. Org. Lett. 2013, 15, 3042
19. Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, C. F. ACS Catal. 2014, 4, 743
20. Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Lett. 2013, 15, 5254
21. Hojo, D.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 5820
22. Shintani, R.; Hayashi, S.-Y.; Murakami, M.; Takeda, M.; Hayashi, T. Org. Lett. 2009, 11, 3754
23. Castaldi, M. P.; Troast, D. M.; Porco, J. A. Org. Lett. 2009, 11, 3362
24. Wang, J.; Crane, E. A.; Scheidt, K. A. Org. Lett. 2011, 13, 3086
25. Ramachary, D. B.; Venkaiah, C.; Madhavachary, R. Org. Lett. 2013, 15, 3042
26. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
27. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691
28. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77
29. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336
30. Rong, Z.-Q.; Zhang, W.; Yang, G.-Q.; You, S.-L. Curr. Org. Chem. 2011, 15, 3077
31. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
32. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53
33. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617
34. Knappke, C. E. I.; Imami, A.; Jacobi von Wangelin, A. ChemCatChem 2012, 4, 937
35. Studer, A.; De Sarkar, S.; Biswas, A.; Samanta, R. C. Chem.-Eur. J. 2013, 19, 4664
36. Hopkinson, M. N.; Richter, C.; Michael, S.; Glorius, F. Nature 2014, 510, 485
37. Chauhan, P.; Enders, D. Angew. Chem., Int. Ed. 2014, 53, 2
38. Shen, L.; Shao, P.; Ye, S. Adv. Synth. Catal. 2011, 353, 1943
39. Shen, L. T.; Jia, W.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 585
40. Shen, L.; Jia, W.; Ye, S. Chin. J. Chem. 2014, 32, 814
41. Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810
42. Chen, X.; Yang, S.; Song, B.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134
43. Yao, C.; Xiao, Z.; Liu, R.; Li, T.; Jiao, W.; Yu, C. Chem.-Eur. J. 2013, 19, 456
44. Xiao, Z.; Yu, C.; Li, T.; Wang, X.; Yao, C. Org. Lett. 2014, 16, 3632
45. Xu, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2013, 15, 5028
46. Liu, R.; Yu, C.; Xiao, Z.; Li, T.; Wang, X.; Xie, Y.; Yao, C. Org. Biomol. Chem. 2014, 12, 1885
47. Donato, L.; Mourot, A.; Davenport, C. M.; Herbivo, C.; Warther, D.; Leonard, J.; Bolze, F.; Nicoud, J.; Kramer, R. H.; Goeldner, M. Angew. Chem., Int. Ed. 2012, 51, 1840
48. Badia, C.; Souard, F.; Vicent, C. J. Org. Chem. 2012, 77, 10870
49. Kawamoto, Y.; Bando, T.; Kamada, F.; Li, Y.; Hashiya, K.; Maeshima, K.; Sugiyama, H. J. Am. Chem. Soc. 2013, 135, 16468
50. Xiao, S.; Wang, Q.; Si, L.; Shi, Y.; Wang, H.; Yu, F.; Zhang, Y.; Li, Y.; Zheng, Y.; Zhang, C. ChemMedChem 2014, 9, 1060