Enantioselective friedel-crafts alkylation of indoles with aromatic αβ-unsaturated aldehydes catalyzed by diphenylprolinol silyl Ether

Synthesis

Volumn , Issue 23, 2009, Pages 3994-4000

  Wang, Zhi Jing ^a   Yang, Jian Guo ^b   Jin, Jun ^a   Lv, Xin ^a   Bao, Weiliang ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b TAIZHOU UNIVERSITY   (China)

Author keywords

unsaturated aldehydes; Aromatic ; Enantioselectivity; Friedel Crafts alkylation; Indoles; Organocatalysis

Indexed keywords

ENANTIOSELECTIVE; FRIEDEL-CRAFTS ALKYLATION; GOOD YIELD; HIGH ENANTIOSELECTIVITY; ORGANOCATALYSIS; SILYL ETHERS; SODIUM BOROHYDRIDES; TRIMETHYL; UNSATURATED ALDEHYDES;

ALDEHYDES; ALKYLATION; CATALYSIS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ETHERS; RATE CONSTANTS; REACTION KINETICS; SODIUM;

AROMATIC COMPOUNDS;

ALDEHYDE; AROMATIC COMPOUND; DIPHENYLPROLINOL SILYL ETHER; INDOLE DERIVATIVE; PHENYL GROUP; PROPANOL; SILANE DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION;

EID: 74049119375     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217038     Document Type: Article

References (67)

1. For a review, see: Olah, G. A.; Khrisnamurti, R.; Surya Prakashi, G. K. In Comprehensive Organic Synthesis, Vol.3; Trost, B. M., Ed.; Pergamon: New York, 1991, 293.
2. (a) Sundberg, R. J. Indoles; Academic Press: San Diego, 1996, 175.
3. (b) Nicolaou, K. C; Snyder, S. A. Classics in Total Synthesis II; Wiley-VCH: Weinheim, 2003.
4. For selected metal-catalyzed procedures, see: (a) Jensen, K. B.; Thorbauge, J.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2001, 40, 160.
5. (b) Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030.
6. (c) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
7. (d) LyIe, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901.
8. (e) Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154.
9. (f) Evans, D. A.; Fandrick, K. R.; Song, H. J. Am. Chem. Soc. 2005, 127, 8942.
10. (g) Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 742.
11. (h) Arai, T.; Yokoyama, N.; Yanagisawa, A. Chem. Eur. J. 2008, 14, 2052.
12. (i) Arai, T.; Yokoyama, N. Angew. Chem. Int. Ed. 2008, 47, 4989.
13. For recent reviews on organocatalysis, see for example: (a) Dalko, P. L.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138.
14. (b) Seayed, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
15. (c) Dalko, P. I. Enantloselective Organocatalysis; Wiley-VCH: Weinheim, 2007.
16. (d) Pellissier, H. Tetrahedron 2007, 63, 9267.
17. (e) Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638.
18. Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
19. (a) Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482.
20. (b) King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kimura, R.; Wu, W.; Gao, Q.; Macor, J. E. Org. Lett. 2005, 7, 3437.
21. (c) Bonini, B. F.; Capito, E.; ComesFranchini, M.; Fochi, M.; Ricci, A.; Zwanenburg, B. Tetrahedron: Asymmetry 2006, 17, 3135.
22. (d)Li, C.; Liu, H.; Liao, J.; Cao, Y.; Liu, X.; Xiao, W. Org. Lett. 2007, 9, 1847.
23. (a) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed. 2005, 44, 6576.
24. (b) Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037.
25. (c) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem. Int. Ed. 2008, 47, 4016.
26. (d) Ganesh, M.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 16464.
27. (a) Li, D.-P.; Guo, Y.-C; Ding, Y.; Xiao, W.-J. Chem. Commun. 2006, 799.
28. (b) Bartoli, G.; Bosco, M.; Cartone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P. Org. Lett. 2007, 9, 1403.
29. (c) Tang, H.-Y.; Lu, A.-D.; Zhou, Z.-H.; Zhao, G,F.; He, L.-N.; Tang, C.-C. Eur. J. Org. Chem. 2008, 1406.
30. (a) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
31. (b) Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484.
32. (c) Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C. Org. Lett. 2007, 9, 2609.
33. (d) Wanner, M. J.; Hauwert, P.; Schoemaker, H. E.; de Gelder, R.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2008, 180.
34. Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem. Int. Ed. 2005, 44, 3086.
35. Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.
36. For the first reports on the use of diarylprolinol silyl ethers, see: (a) Mango, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 794.
37. (b) Marigo, M.; Fielenbach, D.; Braunton, A.; Kjasgaard, A.; Jørgensen, K. A. Angew. Chem, Int. Ed. 2005, 44, 3703.
38. (c) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem. Int. Ed. 2005, 44, 4212.
39. For selected diarylprolinol silyl ethers catalyzed α- functionalization of aldehydes, see: (a) Mossé, S.; Alexakis, A. Org. Lett. 2005, 7, 4361.
40. (b) Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2006, 128, 6804.
41. (c) Ibrahem, I.; Zhao, G.-L.; Cordóva, A. Chem. Eur. J. 2007, 13, 683.
42. (d) Aleman, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jørgensen, K. A. Angew. Chem Int. Ed. 2007, 46, 5520.
43. (e) Tiecco, M.; Carlone, A.; Sternativo, S.; Marini, F.; Bartoli, G.; Melchiorre, P. Angew. Chem. Int. Ed. 2007, 46, 6882.
44. (f) Palomo, C.; Vera, S.; Velila, I.; Mielgo, A.; GomezBengoa, E. Angew. Chem. Int. Ed. 2007, 46, 8054.
45. (g) Hayashi, Y.; Itoh, T.; Ohkubo, M.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 4722.
46. (h) Chi, Y.; Guo, L.; Kopf, N. A.; Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 5608.
47. (i) Shibatomi, K.; Yamamoto, H. Angew. Chem. Int. Ed. 2008, 47, 5796.
48. For selected diarylprolinol silyl ethers catalyzed β- functionalization and γ-functionalization of α,β-unsaturated aldehydes, see: (a) Marigo, M.; Schulte, T.; Frenzen, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
49. (b) Gotoh, H.; Masui, R.; Ogino, H.; Shoji, M.; Hayashi, Y. Angew. Chem. Int. Ed. 2006, 45, 6853.
50. (c) Ibrahem, I.; Rios, R.; Vesely, J.; Zhao, G.; Cordóva, A. Chem. Commun. 2007, 849.
51. (d) Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem. Int. Ed. 2007, 46, 4504.
52. (e) Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Cordóva, A. Angew. Chem. Int. Ed. 2007, 46, 4507.
53. (f) Wang, Y.; Li, P.; Liang, X.; Zhang, T. Y.; Ye, J. Chem. Commun. 2008, 1232.
54. (g) Hayashi, Y.; Samanta, S.; Gotoh, H.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 6634.
55. (h) Zhao, G.-L.; Rios, R.; Vesely, J.; Eriksson, L.; Cordóva, A. Angew. Chem. Int. Ed, 2008, 47, 8468.
56. For selected diarylprolinol silyl ethers catalyzed cascade, tandem, domino and multicomponent reactions, see: (a) Enders, D.; Huttl, M. R. M.; Grondai, C.; Raabe, G. Nature 2006, 441, 861.
57. (b) Brandau, S.; Maerten, E.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
58. (c) Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem. Int. Ed. 2007, 46, 4922.
59. (d) Reyes, E.; Jiang, H.; Milelli, A.; Eisner, P.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem Int. Ed. 2007, 46, 9202.
60. (e) Sunden, H.; Rios, R.; Ibrahem, I.; Zhao, G.; Eriksson, L.; Cordóva, A. Adv. Synth. Catal. 2007, 349, 827.
61. (f)Xie, H.;Zu, L.;Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 729, 10886.
62. (g) Cabrera, S.; Aleman, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2008, 47, 121.
63. (h) Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 4012.
64. (i) Enders, D.; Wang, C.; Bats, J. W. Angew. Chem. Int. Ed. 2008, 47, 7539.
65. For recent reviews on diarylprolinol silyl ethers, see: (a) Palomo, C.; Mielgo, A. Angew. Chem. Int. Ed. 2006, 45, 7876.
66. (b) Mielgo, A.; Palomo, C. Chem. Asian J. 2008, 3, 922.
67. After our original submission of this manuscript to another journal on the 1lth of March, a paper by Wang and coworkers appeared on the web on 17th March, see: Hong, L.; Wang, L.; Chen, C.; Zhang, B.; Wang, R. Adv. Synth. Catal. 2009, 351, 772.