Organocatalytic chemo-, (E/Z)- and enantioselective formal alkenylation of indole-derived hydroxylactams using o -hydroxystyrenes as a source of alkenyl group

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 7141-7151

  Zhang, Hong Hao ^a   Wang, Yue Ming ^a   Xie, Yuan Wei ^a   Zhu, Zi Qi ^a   Shi, Feng ^a   Tu, Shu Jiang ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL ACTIVATION; ENANTIOSELECTIVITY; HYDROGEN BONDS; PYRIDINE;

CARBOLINE DERIVATIVES; DUAL ACTIVATION; ELIMINATION REACTION; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; HYDROGEN BOND INTERACTION; STEREO-SELECTIVE; STEREOGENIC CENTERS;

ALKENYLATION;

ALKENYL GROUP; BETA CARBOLINE DERIVATIVE; HYDROGEN; HYDROXYL GROUP; HYDROXYLACTAM DERIVATIVE; LACTAM DERIVATIVE; O HYDROXYSTYRENE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKENYLATION; ARTICLE; BIOTRANSFORMATION; CATALYST; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL PHENOMENA; CHEMICAL REACTION KINETICS; CHEMOSELECTIVITY; CHIRALITY; CONTROLLED STUDY; ELIMINATION REACTION; ENANTIOSELECTIVITY; HYDROGEN BOND; ORGANOCATALYST; SYNTHESIS;

EID: 84905393927     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501293m     Document Type: Article

References (64)

1. For a review, see: Negishi, E.; Huang, Z.-H.; Wang, G.-W.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474
2. Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 994
3. Cui, Z.; Chen, Y.-J.; Gao, W.-Y.; Feng, C.-G.; Lin, G.-Q. Org. Lett. 2014, 16, 1016
4. Stevens, J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 11756
5. Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2007, 129, 4908
6. Tomita, D.; Kanai, M.; Shibasaki, M. Chem.-Asian J. 2006, 1, 161
7. Aikawa, K.; Hioki, Y.; Mikami, K. J. Am. Chem. Soc. 2009, 131, 13922
8. Motoki, R.; Tomita, D.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 8083
9. Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 4138
10. Ji, J.-X.; Qiu, L.-Q.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589
11. Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257
12. Oi, S.; Sato, T.; Inoue, Y. Tetrahedron Lett. 2004, 45, 5055
13. Nicolaou, K. C.; Tang, W.; Dagneau, P.; Faraoni, R. Angew. Chem., Int. Ed. 2005, 44, 3874
14. Mahoney, S. J.; Dumas, A. M.; Fillion, E. Org. Lett. 2009, 11, 5346
15. Robert, T.; Velder, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2008, 47, 7718
16. Vuagnoux-dAugustin, M.; Alexakis, A. Chem.-Eur. J. 2007, 13, 9647
17. Hawner, C.; Li, K.; Cirriez, V.; Alexakis, A. Angew. Chem., Int. Ed. 2008, 47, 8211
18. Müller, D.; Tissot, M.; Alexakis, A. Org. Lett. 2011, 13, 3043
19. Mueller, D.; Alexakis, A. Chem. Commun. 2012, 48, 12037
20. Lou, S.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 5010
21. Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302
22. Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis; Academic Press/Elsevier Science: Amsterdam, 2005.
23. de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012, 41, 3969
24. Hashimoto, T.; Kimura, H.; Maruoka, K. Angew. Chem., Int. Ed. 2010, 49, 6844
25. Nielsen, M.; Borch, J. C.; Paixao, M. W.; Holub, N.; Jorgensen, K. A. J. Am. Chem. Soc. 2009, 131, 10581
26. Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278
27. Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761
28. OConnor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532
29. Spindola, H. M.; Vendramini-Costa, D. B.; Rodrigues, M. T.; Foglio, M. A.; Pilli, R. A.; Carvalho, J. E. Pharmacol., Biochem. Behav. 2012, 102, 133
30. Barbara, H.; Michael, D.; Patrick, M.; Astrid, M. S.; Sherif, A. F. R.; Hussein, E. S.; Peter, M. S.; Dirk, R. R.; Matthias, U. K.; Jochen, L. J. Med. Chem. 2006, 49, 760
31. Li, Z.; Li, J.; Yang, N.; Chen, Y.; Zhou, Y.; Ji, X.; Zhang, L.; Wang, J.-F.; Xie, X.; Liu, H. J. Org. Chem. 2013, 78, 10802
32. Yeung, B. K. S.; Zou, B.; Rottmann, M.; Lakshminarayana, S. B.; Ang, S. H.; Leong, S. Y.; Tan, J.; Wong, J.; Keller-Maerki, S.; Fischli, C.; Goh, A.; Schmitt, E. K.; Krastel, P.; Francotte, E.; Kuhen, K.; Plouffe, D.; Henson, K.; Wagner, T.; Winzeler, E. A.; Petersen, F.; Brun, R.; Dartois, V.; Diagana, T. T.; Keller, T. H. J. Med. Chem. 2010, 53, 5155
33. Chinigo, G. M.; Paige, M.; Grindrod, S.; Hamel, E.; Dakshanamurthy, S.; Chruszcz, M.; Minor, W.; Brown, M. L. J. Med. Chem. 2008, 51, 4620
34. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
35. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
36. Akiyama, T. Chem. Rev. 2007, 107, 5744
37. Terada, M. Chem. Commun. 2008, 35, 4097
38. Terada, M. Synthesis 2010, 1929
39. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156
40. Yin, Q.; Wang, S.-G.; You, S.-L. Org. Lett. 2013, 15, 2688
41. Shi, F.; Zhu, R.-Y.; Liang, X.; Tu, S.-J. Adv. Synth. Catal. 2013, 355, 2447
42. Shi, F.; Tan, W.; Zhu, R.-Y.; Xing, G.-J.; Tu, S.-J. Adv. Synth. Catal. 2013, 355, 1605
43. Shi, F.; Zhu, R.-Y.; Dai, W.; Wang, C.-S.; Tu, S.-J. Chem.-Eur. J. 2014, 20, 2597
44. Shi, F.; Xing, G.-J.; Tao, Z.-L.; Luo, S.-W.; Tu, S.-J.; Gong, L.-Z. J. Org. Chem. 2012, 77, 6970
45. Shi, F.; Xing, G.-J.; Zhu, R.-Y.; Tan, W.; Tu, S.-J. Org. Lett. 2013, 15, 128
46. Yu, S.-Y.; Zhang, H.; Gao, Y.; Mo, L.; Wang, S.; Yao, Z.-J. J. Am. Chem. Soc. 2013, 135, 11402
47. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193
48. Wang, X.-W.; List, B. Angew. Chem., Int. Ed. 2008, 47, 1119
49. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
50. Li, C.-Q.; Barbara, V.-M.; Xiao, J.-L. J. Am. Chem. Soc. 2009, 131, 6967
51. Li, C.-Q.; Wang, C.; Barbara, V.-M.; Xiao, J.-L. J. Am. Chem. Soc. 2008, 130, 14450
52. Terada, M.; Tanaka, H.; Sorimachi, K. J. Am. Chem. Soc. 2009, 131, 3430
53. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496
54. Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8707
55. Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620
56. Rueping, M.; Uria, U.; Lin, M.-Y.; Atodiresei, I. A. J. Am. Chem. Soc. 2011, 133, 3732
57. Eider, A.; Nuria, S.; Esther, L. J. Org. Chem. 2012, 77, 2986
58. Tsubasa, I.; Kiyosei, T.; Toshiyuki, S.; Yoshiji, T. Org. Lett. 2009, 11, 2425
59. Čorić, I.; Müller, S.; List, B. J. Am. Chem. Soc. 2010, 132, 17370
60. Xing, C.; Liao, Y.; Ng, J.; Hu, Q. J. Org. Chem. 2011, 76, 4125
61. Xu, B.; Zhu, S.; Xie, X.; Shen, J.; Zhou, Q. Angew. Chem., Int. Ed. 2011, 50, 11483
62. Xu, F.; Huang, D.; Han, C.; Shen, W.; Lin, X. F.; Wang, Y. J. Org. Chem. 2010, 75, 8677
63. Elias, X.; Pleixats, R.; Man, M. W. C. Tetrahedron 2008, 64, 6770
64. Chatterjee, A. K.; Toste, F. D.; Goldberg, S. D.; Grubbs, R. H. Pure Appl. Chem. 2003, 75, 421