N-Heterocyclic Carbene-Catalyzed Formal [3 + 2] Annulation of α-Bromoenals with 3-Aminooxindoles: A Stereoselective Synthesis of Spirooxindole γ-Butyrolactams

Journal of Organic Chemistry

Volumn 80, Issue 22, 2015, Pages 11593-11597

  Jiang, Delu ^a   Dong, Shuding ^a   Tang, Weifang ^a   Lu, Tao ^a   Du, Ding ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

BUTYROLACTAMS; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; N-HETEROCYCLIC CARBENES; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS; SYNTHETIC APPROACH;

ORGANIC COMPOUNDS;

2 PYRROLIDONE DERIVATIVE; CARBENE; OXINDOLE; TERT BUTYL 1 METHYL 2,5' DIOXO 3' (MTOLYL) SPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 1 METHYL 2,5' DIOXO 3' (PTOLYL) SPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 1 METHYL 2,5' DIOXO 3' PHENYLSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 1 METHYL 3' (NAPHTHALEN 1 YL) 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 1,5 DIMETHYL 2,5' DIOXO 3' PHENYLSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (2 CHLOROPHENYL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (4 BROMOPHENYL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (4 CHLOROPHENYL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (4 FLUOROPHENYL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (4 METHOXYPHENYL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 3' (FURAN 2 YL) 1 METHYL 2,5' DIOXOSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; TERT BUTYL 5 FLUORO 1 METHYL 2,5' DIOXO 3' PHENYLSPIRO[INDOLINE 3,2' PYRROLIDINE] 1' CARBOXYLATE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYST; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 84947924199     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02188     Document Type: Article

References (60)

1. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748 10.1002/anie.200701342
2. Santos, M. M. M. Tetrahedron 2014, 70, 9735 10.1016/j.tet.2014.08.005
3. Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, C. F. ACS Catal. 2014, 4, 743 10.1021/cs401172r
4. Yu, B.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2015, 97, 673 10.1016/j.ejmech.2014.06.056
5. Yu, B.; Yu, Z.; Qi, P.-P.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2015, 95, 35 10.1016/j.ejmech.2015.03.020
6. Kathirvelan, D.; Haribabu, J.; Reddy, B. S. R.; Balachandran, C.; Duraipandiyan, V. Bioorg. Med. Chem. Lett. 2015, 25, 389 10.1016/j.bmcl.2014.10.099
7. Wu, G.; Ouyang, L.; Liu, J.; Zeng, S.; Huang, W.; Han, B.; Wu, F.; He, G.; Xiang, M. Mol. Diversity 2013, 17, 271 10.1007/s11030-013-9432-3
8. Haddad, S.; Boudriga, S.; Akhaja, T. N.; Raval, J. P.; Porzio, F.; Soldera, A.; Askri, M.; Knorr, M.; Rousselin, Y.; Kubicki, M. M.; Rajani, D. New J. Chem. 2015, 39, 520 10.1039/C4NJ01008F
9. Kumar, A.; Gupta, G.; Bishnoi, A. K.; Saxena, R.; Saini, K. S.; Konwar, R.; Kumar, S.; Dwivedi, A. Bioorg. Med. Chem. 2015, 23, 839 10.1016/j.bmc.2014.12.037
10. Arun, Y.; Saranraj, K.; Balachandran, C.; Perumal, P. T. Eur. J. Med. Chem. 2014, 74, 50 10.1016/j.ejmech.2013.12.027
11. Girgis, A. S. Eur. J. Med. Chem. 2009, 44, 91 10.1016/j.ejmech.2008.03.013
12. Rajesh, S. M.; Perumal, S.; Menendez, J. C.; Yogeeswari, P.; Sriram, D. MedChemComm 2011, 2, 626 10.1039/c0md00239a
13. Shi, F.; Tao, Z.-L.; Luo, S.-W.; Tu, S.-J.; Gong, L.-Z. Chem.-Eur. J. 2012, 18, 6885 10.1002/chem.201200358
14. Tian, L.; Hu, X.-Q.; Li, Y.-H.; Xu, P.-F. Chem. Commun. 2013, 49, 7213 10.1039/c3cc43755h
15. Menon, R. S.; Biju, A. T.; Nair, V. Chem. Soc. Rev. 2015, 44, 5040 10.1039/C5CS00162E
16. Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307 10.1021/acs.chemrev.5b00060
17. Mahatthananchai, J.; Bode, J. W. Acc. Chem. Res. 2014, 47, 696 10.1021/ar400239v
18. Albanese, D. C. M.; Gaggero, N. Eur. J. Org. Chem. 2014, 2014, 5631 10.1002/ejoc.201402024
19. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906 10.1039/c3cs35522e
20. De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.-Eur. J. 2013, 19, 4664 10.1002/chem.201203707
21. Chen, X.-Y.; Ye, S. Org. Biomol. Chem. 2013, 11, 7991 10.1039/c3ob41469h
22. Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686 10.1002/anie.201203704
23. Zeitler, K. Org. Lett. 2006, 8, 637 10.1021/ol052826h
24. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810 10.1021/ja103631u
25. Zhu, Z.-Q.; Zheng, X.-L.; Jiang, N.-F.; Wan, X.; Xiao, J.-C. Chem. Commun. 2011, 47, 8670 10.1039/c1cc12778k
26. Lu, Y.; Tang, W.; Zhang, Y.; Du, D.; Lu, T. Adv. Synth. Catal. 2013, 355, 321 10.1002/adsc.201200716
27. Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494 10.1021/cs300020t
28. Zhou, B.; Luo, Z.; Li, Y. Chem.-Eur. J. 2013, 19, 4428 10.1002/chem.201203436
29. Du, D.; Hu, Z.; Jin, J.; Lu, Y.; Tang, W.; Wang, B.; Lu, T. Org. Lett. 2012, 14, 1274 10.1021/ol300148f
30. Romanov-Michailidis, F.; Besnard, C.; Alexakis, A. Org. Lett. 2012, 14, 4906 10.1021/ol3022287
31. De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266 10.1002/anie.201004593
32. Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 9433 10.1002/anie.201204145
33. Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378 10.1021/ol202272t
34. Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13, 4080 10.1021/ol201595f
35. Biswas, A.; De Sarkar, S.; Tebben, L.; Studer, A. Chem. Commun. 2012, 48, 5190 10.1039/c2cc31501g
36. Bera, S.; Samanta, R. C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 9622 10.1002/anie.201405200
37. Mao, J.-H.; Wang, Z.-T.; Wang, Z.-Y.; Cheng, Y. J. Org. Chem. 2015, 80, 6350 10.1021/acs.joc.5b00784
38. Xie, D.; Yang, L.; Lin, Y.; Zhang, Z.; Chen, D.; Zeng, X.; Zhong, G. Org. Lett. 2015, 17, 2318 10.1021/acs.orglett.5b00726
39. Hu, S.; Wang, B.; Zhang, Y.; Tang, W.; Fang, M.; Lu, T.; Du, D. Org. Biomol. Chem. 2015, 13, 4661 10.1039/C5OB00176E
40. Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2013, 135, 58 10.1021/ja310449k
41. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694 10.1021/ja111067j
42. Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592 10.1002/anie.201303247
43. Candish, L.; Levens, A.; Lupton, D. W. J. Am. Chem. Soc. 2014, 136, 14397 10.1021/ja508542n
44. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176 10.1021/ja905501z
45. Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134 10.1002/adsc.201100622
46. Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chem.-Eur. J. 2012, 18, 1914 10.1002/chem.201103358
47. Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089 10.1002/adsc.201300219
48. Zhang, H.-M.; Jia, W.-Q.; Liang, Z.-Q.; Ye, S. Asian J. Org. Chem. 2014, 3, 462 10.1002/ajoc.201400010
49. Gao, Z.-H.; Chen, X.-Y.; Zhang, H.-M.; Ye, S. Chem. Commun. 2015, 51, 12040 10.1039/C5CC04593B
50. Ni, Q.; Song, X.; Raabe, G.; Enders, D. Chem.-Asian J. 2014, 9, 1535 10.1002/asia.201402052
51. Yetra, S. R.; Roy, T.; Bhunia, A.; Porwal, D.; Biju, A. T. J. Org. Chem. 2014, 79, 4245 10.1021/jo500693h
52. Yetra, S. R.; Kaicharla, T.; Kunte, S. S.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2013, 15, 5202 10.1021/ol4026155
53. Zhang, H.-R.; Dong, Z.-W.; Yang, Y.-J.; Wang, P.-L.; Hui, X.-P. Org. Lett. 2013, 15, 4750 10.1021/ol4024985
54. Chen, X.-Y.; Gao, Z.-H.; Song, C.-Y.; Zhang, C.-L.; Wang, Z.-X.; Ye, S. Angew. Chem., Int. Ed. 2014, 53, 11611 10.1002/anie.201407469
55. Zhao, Q.; Huang, W.; Han, B.; Wang, B.; Leng, H.-J.; Peng, C. RSC Adv. 2015, 5, 26972 10.1039/C5RA01254F
56. Zhang, Y.; Lu, Y.; Tang, W.; Lu, T.; Du, D. Org. Biomol. Chem. 2014, 12, 3009 10.1039/c4ob00145a
57. Xu, J.; Hu, S.; Lu, Y.; Dong, Y.; Tang, W.; Lu, T.; Du, D. Adv. Synth. Catal. 2015, 357, 923 10.1002/adsc.201401070
58. Zhang, B.; Feng, P.; Sun, L.-H.; Cui, Y.; Ye, S.; Jiao, N. Chem.-Eur. J. 2012, 18, 9198 10.1002/chem.201201375
59. Lv, H.; Tiwari, B.; Mo, J.; Xing, C.; Chi, Y. R. Org. Lett. 2012, 14, 5412 10.1021/ol302475g
60. Emura, T.; Esaki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559 10.1021/jo061541v