Multistep one-pot synthesis of enantioenriched polysubstituted cyclopenta[b] indoles

Angewandte Chemie - International Edition

Volumn 51, Issue 4, 2012, Pages 1059-1062

  Xu, Biao ^a   Guo, Zhi Lei ^a   Jin, Wan Yan ^a   Wang, Zhi Ping ^a   Peng, Yun Gui ^a   Guo, Qi Xiang ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

alkylations; indoles; multistep reactions; one pot syntheses; organocatalysis

Indexed keywords

DIASTEREOSELECTIVITIES; HIGH YIELD; INDOLES; MULTI-STEP; MULTISTEP REACTIONS; ONE POT; ONE-POT SYNTHESES; ONE-POT SYNTHESIS; ORGANOCATALYSIS;

ALDEHYDES; ALKYLATION; CATALYSIS; REACTION KINETICS;

LEAD COMPOUNDS;

ALDEHYDE; CYCLOPENTANE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLOPENTANES; INDOLES; STEREOISOMERISM;

EID: 84862909163     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107308     Document Type: Article

References (56)

1. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875
2. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786
3. Angew. Chem. Int. Ed. 2009, 48, 9608
4. A. J. Kochanowska-Karamyan, M. T. Hamann, Chem. Rev. 2010, 110, 4489.
5. For a review, see:, P. S. steyn, R. Vleggar, Fortschr. Chem. Org. Naturst. 1985, 48, 1.
6. A. A. Asselin, L. G. Humber, J. Komlossy, J. Med. Chem. 1976, 19, 792
7. A. A. Asselin, L. G. Humber, T. A. Dobson, U.S. Patent 4057599, 1977
8. A. A. Failli, R. J. Steffan, A. F. Kreft, T. J. Caggiano, C. E. Caufield, U.S. Patent 5830911, 1998
9. Y. C. Kong, K. H. Ng, K. H. Wat, A. Wong, I. F. Saxena, K. F. Cheng, P. P. H. But, H. T. Chang, Planta Med. 1985, 51, 304
10. K. F. Cheng, M. K. Cheung, Y. C. Kong, Aust. J. Chem. 1997, 50, 349
11. G. Dionne, A. A. Asselin, L. G. Humber, U.S. Patent 4235903, 1980.
12. J. P. Kondaji, K. Venkatesh, K. E. Jemes, WO 2009140448A1, 2009
13. M. C. Hillier, J. F. Marcoux, D. Zhao, E. J. J. Grabowski, A. E. McKeiwn, R. D. Tillyer, J. Org. Chem. 2005, 70, 8385
14. K. R. Campos, M. Journet, S. Lee, E. J. J. Grabowski, R. D. Tillyer, J. Org. Chem. 2005, 70, 268.
15. K. F. Cheng, Y. C. Kong, T. Y. Chan, J. Chem. Soc. Chem. Commun. 1985, 48
16. J. H. Sheu, Y. K. Chen, H. F. Chung, S. F. Lin, P. J. Sung, J. Chem. Soc. Perkin Trans. 1 1998, 1959; for yuehchukene anologies, see
17. K. F. Cheng, T. T. Chan, T. F. Lai, Y. C. Kong, J. Chem. Soc. Perkin Trans. 1 1988, 3317
18. K. F. Cheng, G. A. Cao, Y. W. Yu, Y. C. Kong, Synth. Commun. 1994, 24, 65.
19. H. Ratni, D. Blum-kaelin, H. Dehmlow, P. Hartman, P. Jablonski, R. Masciadri, C. Maugeais, A. Patiny-Adam, N. Panday, M. Wright, Bioorg. Med. Chem. Lett. 2009, 19, 1654
20. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578
21. K. Saito, H. Sogou, T. Suga, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2011, 133, 689
22. Q. Xiao, P. E. Floreancig, Org. Lett. 2008, 10, 1139
23. N.-W. Tsent, M. Lautens, J. Org. Chem. 2009, 74, 1809
24. E. P. Balskus, C. T. Walsh, J. Am. Chem. Soc. 2009, 131, 14648
25. C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358.
26. F. Churruca, M. Fousteris, Y. Ishikawa, M. V. W. Rekowski, C. Hounsou, T. Surrey, A. Giannis, Org. Lett. 2010, 12, 2096
27. A. Shafiee, V. Upadhyay, E. G. Corley, M. Biba, D. Zhao, J.-F. Marcoux, K. R. Campos, M. Journet, A. O. King, R. D. Larsen, E. J. J. Grabowski, R. P. Volante, R. D. Tillyer, Tetrahedron: Asymmetry 2005, 16, 3094
28. B. Han, Y.-C. Xiao, Y. Yao, Y.-C. Chen, Angew. Chem. 2010, 122, 10387
29. Angew. Chem. Int. Ed. 2010, 49, 10189.
30. J. A. Schiffner, T. H. Wöste, M. Oestreich, Eur. J. Org. Chem. 2010, 174.
31. Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, L.-Z. Gong, Org. Lett. 2009, 11, 4620.
32. Å. Albrecht, H. Jiang, K. A. J̀rgensen, Angew. Chem. 2011, 123, 8642
33. Angew. Chem. Int. Ed. 2011, 50, 8492
34. D. Enders, C. Grondal, H. R. M. Matthias, Angew. Chem. 2007, 119, 1590
35. Angew. Chem. Int. Ed. 2007, 46, 1570; For selected examples of one-pot multistep reactions, see
36. P. Cao, X.-L. Sun, B.-H. Zhu, Q. Shen, Z. Xie, Y. Tang, Org. Lett. 2009, 11, 3048
37. X. Wang, K. Ding, Chem. Eur. J. 2006, 12, 4568
38. A. Sniady, M. W. Bedore, T. F. Jamison, Angew. Chem. 2011, 123, 2203
39. Angew. Chem. Int. Ed. 2011, 50, 2155
40. P. Li, S. L. Buchwald, Angew. Chem. 2011, 123, 6520
41. Angew. Chem. Int. Ed. 2011, 50, 6396.
42. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835
43. Angew. Chem. Int. Ed. 2008, 47, 8707
44. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339
45. Angew. Chem. Int. Ed. 2009, 48, 1313
46. A. Gualandi, E. Emer, M. G. Capdevila, P. G. Cozzi, Angew. Chem. 2011, 123, 7988
47. Angew. Chem. Int. Ed. 2011, 50, 7842
48. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
49. Angew. Chem. Int. Ed. 2010, 49, 9685
50. F. Benfatti, E. Benedetto, P. G. Cozzi, Chem. Asian J. 2010, 5, 2047
51. L. Zhang, L. Cui, X. Li, J. Li, S. Luo, J.-P. Cheng, Chem. Eur. J. 2010, 16, 2045
52. A. R. Brown, W.-H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 9286.
53. F.-L. Sun, M. Zeng, Q. Gu, S.-L. You, Chem. Eur. J. 2009, 15, 8709
54. C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557
55. Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484
56. F.-L. Sun, X.-J. Zheng, Q. Gu, Q.-L. He, S.-L. You, Eur. J. Org. Chem. 2010, 47.