Construction of vicinal all-carbon quaternary stereocenters by catalytic asymmetric alkylation reaction of 3-bromooxindoles with 3-substituted indoles: Total synthesis of (+)-perophoramidine

Journal of the American Chemical Society

Volumn 135, Issue 38, 2013, Pages 14098-14101

  Zhang, Hailong ^a   Hong, Liang ^a   Kang, Hong ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ALKYLATION; CATALYTIC REACTIONS; ENANTIOCONTROL; QUATERNARY STEREOCENTERS; REACTION PARTNERS; TOTAL SYNTHESIS;

CATALYSIS; SYNTHESIS (CHEMICAL);

CARBON;

AMIDINE; CARBON; INDOLE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DIASTEREOISOMER; ELECTRON; ENANTIOMER; ENANTIOSELECTIVITY; SYNTHESIS;

ALKYLATION; CATALYSIS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; INDOLES; STEREOISOMERISM;

EID: 84884897387     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408336v     Document Type: Article

References (56)

1. Dalsgaard, P. W.; Blunt, J. W.; Munro, M. H. G.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258
2. Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. J. Nat. Prod. 2004, 67, 78
3. Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci., Biotechnol., Biochem. 2004, 68, 753
4. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355
5. Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124
6. Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447
7. Siengalewicz, P.; Gaich, T.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 8170
8. Ishida, T.; Takemoto, Y. Tetrahedron 2013, 69, 4517
9. Schammel, A.-W.; Chiou, G.; Garg, N.-K. Org. Lett. 2012, 14, 4556
10. Wu, H.; Xiao, X.; Qin, Y. Synlett 2011, 7, 907
11. Seashore-Ludlow, B.; Somfai, P. Org. Lett. 2010, 12, 3732
12. Evans, M. A.; Sacher, J. R.; Weinreb, S. M. Tetrahedron 2009, 65, 6712
13. George, J. H.; Adlington, R. M. Synlett 2008, 4, 2093
14. Crawley, S.; Funk, R. L. Org. Lett. 2006, 8, 3995
15. Seo, J. H.; Artman, G. D.; Weinreb, S. M. J. Org. Chem. 2006, 71, 8891
16. Yang, J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006, 8, 2187
17. May, J. A.; Stoltz, B. M. Tetrahedron 2006, 62, 5262
18. Crawley, S.; Funk, R. L. Org. Lett. 2003, 5, 3169
19. Artman, G. D.; Weinreb, S. M. Org. Lett. 2003, 5, 1523
20. May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203
21. Belmar, J.; Funk, R. L. J. Am. Chem. Soc. 2012, 134, 16941
22. Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008
23. Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000
24. Zuo, Z. W.; Xie, W. Q.; Ma, D. W. J. Am. Chem. Soc. 2010, 132, 13226
25. Yang, J.; Wu, H. X.; Shen, L. Q.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794
26. Wu, H. X.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052
27. Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2006, 45, 4317
28. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068
29. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
30. Shimizu, M. Angew. Chem., Int. Ed. 2011, 50, 5998
31. Wang, B.; Tu, Y. Q. Acc. Chem. Res. 2011, 44, 1207
32. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295
33. Jautze, S.; Peters, R. Synthesis 2010, 365
34. Bella, M.; Gasperi, T. Synthesis 2009, 1583
35. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 72, 5969
36. Mohr, J. T.; Stoltz, B. M. Chem. Asian J. 2007, 2, 1476
37. Trost, B. M.; Jiang, C. Synthesis 2006, 369
38. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, 2005.
39. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
40. Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105
41. Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591
42. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
43. Fuji, K. Chem. Rev. 1993, 93, 2037
44. Trost, B. M.; Osipov, M. Angew. Chem., Int. Ed. 2013, 52, 9176
45. Du, C.; Li, L.; Li, Y.; Xie, Z. Angew. Chem., Int. Ed. 2009, 48, 7853
46. Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943
47. Corey, E. J.; Lin, S. J. Am. Chem. Soc. 1996, 118, 8765
48. Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677
49. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431
50. Zuo, J.; Liao, Y.-H; Zhang, X.; Yuan, W.-C. J. Org. Chem. 2012, 77, 11325
51. Liao, Y.-H.; Wu, Z.-J.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Chem.-Eur. J. 2012, 18, 8916
52. Ma, S.; Han, X.; Krishnan, S.; Virgil, S. C.; Stoltz, B. M. Angew. Chem., Int. Ed. 2009, 48, 8037
53. Li, W.; Liu, X.; Mao, Z.; Chen, Q.; Wang, R. Org. Biomol. Chem. 2012, 10, 4767
54. Wilckens, K.; Duhs, M.-A.; Lentz, D.; Czekelius, C. Eur. J. Org. Chem. 2011, 76, 5441
55. Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2011, 17, 14922
56. Nakamura, A.; Lectard, S.; Hashizume, D.; Hamashima, Y.; Sodeoka, M. J. Am. Chem. Soc. 2010, 132, 4036