Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines

Journal of Organic Chemistry

Volumn 80, Issue 17, 2015, Pages 8836-8842

  Zheng, Jianfeng ^a   Lin, Lili ^a   Fu, Kai ^a   Zheng, Haifeng ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a,b  

^a Sichuan University   (China)

^b Collaborative Innovation Center of Chemical Science and Engineering ^*  (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; OLEFINS; ZINC COMPOUNDS;

CATALYTIC SYSTEM; DIELS-ALDER REACTION; STEREOCENTERS; STEREOSPECIFIC MANNER; ZN COMPLEX;

CHEMICAL REACTIONS;

ALKADIENE; CYCLOHEXANE DERIVATIVE; INDOLE DERIVATIVE; METHYLENEINDOLINE DERIVATIVE; SPIRO[CYCLOHEX[3]ENE 1,3' INDOLINE] 1' CARBOXYLATE 2, 2' DIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CIRCULAR DICHROISM; DIASTEREOISOMER; DIELS ALDER REACTION; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; STEREOSPECIFICITY; SYNTHESIS;

EID: 84940993861     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01318     Document Type: Article

References (53)

1. Edmondson, S.; Danishefsky, S. J.; Lorenzino, L. S.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147 10.1021/ja983788i
2. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36 10.1002/anie.200390048
3. Lo, M. M.-C.; Neumann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 16077 10.1021/ja045089d
4. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748 10.1002/anie.200701342
5. Kotha, S.; Deb, A. C.; Lahiri, K.; Manivannan, E. Synthesis 2009, 165 10.1055/s-0028-1083300
6. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104 10.1021/cr300135y
7. Shen, K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Sci. 2012, 3, 327 10.1039/C1SC00544H
8. Hanhan, N. V.; Ball-Jones, N. R.; Tran, N. T.; Franz, A. K. Angew. Chem., Int. Ed. 2012, 51, 989 10.1002/anie.201105739
9. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023 10.1002/adsc.201200808
10. Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390 10.1021/cr400215u
11. Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571 10.1021/jo00043a005
12. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209 10.1002/ejoc.200300050
13. Beccalli, E. M.; Clerici, F.; Gelmi, M. L. Tetrahedron 2003, 59, 4615 10.1016/S0040-4020(03)00627-6
14. Feldman, K. S.; Vidulova, D. B. Org. Lett. 2004, 6, 1869 10.1021/ol0493406
15. Liu, J.-J.; Zhang, Z.; Hoffmann-LaRoche, A. G. Spiroindolinone derivatives. PCT Int. Appl. WO2008055812, May 15, 2008.
16. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003 10.1055/s-0029-1216975
17. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381 10.1002/adsc.201000161
18. Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247 10.1039/c2cs35100e
19. Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, C. F., III. ACS Catal. 2014, 4, 743 10.1021/cs401172r
20. Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200 10.1002/anie.200903192
21. Companyó, X.; Zea, A.; Alba, A.-N. R.; Mazzanti, A.; Moyanoa, A.; Rios, R. Chem. Commun. 2010, 46, 6953 10.1039/c0cc01522a
22. Zhou, B.; Yang, Y. X.; Shi, J. J.; Luo, Z.; Li, Y. C. J. Org. Chem. 2013, 78, 2897 10.1021/jo302655u
23. Sun, Q.-S.; Chen, X.-Y.; Zhu, H.; Lin, H.; Sun, X.-W.; Lin, G.-Q. Org. Chem. Front. 2015, 2, 110 10.1039/C4QO00299G
24. Wei, Q.; Gong, L.-Z. Org. Lett. 2010, 12, 1008 10.1021/ol100020v
25. Jiang, K.; Jia, Z.-J.; Chen, S.; Wu, L.; Chen, Y.-C. Chem.-Eur. J. 2010, 16, 2852 10.1002/chem.200903009
26. Wang, L.-L.; Peng, L.; Bai, J.-F.; Jia, L.-N.; Luo, X.-Y.; Huang, Q. C.; Xu, X.-Y.; Wang, L.-X. Chem. Commun. 2011, 47, 5593 10.1039/c1cc11223f
27. Lan, Y.-B.; Zhao, H.; Liu, Z.-M.; Liu, G.-G.; Tao, J.-C.; Wang, X.-W. Org. Lett. 2011, 13, 4866 10.1021/ol201943g
28. Wu, H.; Wang, Y.-M. Chem.-Eur. J. 2014, 20, 5899 10.1002/chem.201402002
29. Ghosh, A. K.; Zhou, B. Tetrahedron Lett. 2013, 54, 2311 10.1016/j.tetlet.2013.02.030
30. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007 10.1021/cr00013a013
31. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z
32. Jia, Z. J.; Jiang, H.; Li, J. L.; Gschwend, B.; Li, Q. Z.; Yin, X.; Groulef, J.; Chen, Y.-C.; Jørgensen, K. A. J. Am. Chem. Soc. 2011, 133, 5053 10.1021/ja1112194
33. Tan, B.; Hernández-Torres, G.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 12354 10.1021/ja203812h
34. Li, G. L.; Liang, T.; Wojtas, L.; Antilla, J. C. Angew. Chem., Int. Ed. 2013, 52, 4628 10.1002/anie.201209295
35. Zheng, H. F.; He, P.; Liu, Y. B.; Zhang, Y. L.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Commun. 2014, 50, 8794 10.1039/C4CC03135K
36. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807 10.1021/ja00832a031
37. Savard, J.; Brassard, P. Tetrahedron Lett. 1979, 20, 4911 10.1016/S0040-4039(01)86747-2
38. Togni, A. Organometallics 1990, 9, 3106 10.1021/om00162a023
39. Fan, Q.; Lin, L. L.; Liu, J.; Huang, Y. Z.; Feng, X. M.; Zhang, G. L. Org. Lett. 2004, 6, 2185 10.1021/ol049364c
40. Lin, L. L.; Liu, X. H.; Feng, X. M. Synlett 2007, 2147 10.1055/s-2007-984917
41. Lin, L. L.; Chen, Z. L.; Yang, X.; Liu, X. H.; Feng, X. M. Org. Lett. 2008, 10, 1311 10.1021/ol8002282
42. Lin, L. L.; Kuang, Y. L.; Liu, X. H.; Feng, X. M. Org. Lett. 2011, 13, 3868 10.1021/ol2013999
43. Zheng, J. F.; Lin, L. L.; Kuang, Y. L.; Zhao, J. N.; Liu, X. H.; Feng, X. M. Chem. Commun. 2014, 50, 994 10.1039/C3CC47800A
44. Du, H. F.; Zhao, D. B.; Ding, K. L. Chem.-Eur. J. 2004, 10, 5964 10.1002/chem.200400515
45. Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2006, 45, 4796 10.1002/anie.200601345
46. Lucas, B. S.; Gopalsamuthiram, V.; Burke, S. D. Angew. Chem., Int. Ed. 2007, 46, 769 10.1002/anie.200603656
47. Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574 10.1021/ar200015s
48. Zheng, K.; Lin, L. L.; Feng, X. M. Huaxue Xuebao 2012, 70, 1785 10.6023/A12070447
49. Liu, X. H.; Lin, L. L.; Feng, X. M. Org. Chem. Front. 2014, 1, 298 10.1039/c3qo00059a
50. Xie, M. S.; Wu, X. X.; Wang, G.; Lin, L. L.; Feng, X. M. Huaxue Xuebao 2014, 72, 856 10.6023/A13121253
51. Zhao, X. H.; Liu, X. H.; Mei, H. J.; Guo, J.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2015, 54, 4032 10.1002/anie.201410814
52. Zhao, J. N.; Fang, B.; Luo, W. W.; Hao, X. Y.; Liu, X. H.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2015, 54, 241 10.1002/anie.201408730
53. www.ccdc.cam.ac.uk/data-request/cif