Highly enantioselective Friedel–Crafts alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes

Chemical Communications

Volumn 48, Issue 74, 2012, Pages 9281-9283

  Liu, Lei ^a   Ma, Hongli ^a   Xiao, Yumei ^a   Du, Fengpei ^a   Qin, Zhaohai ^a   Li, Nan ^a   Fu, Bin ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GAMMA UNSATURATED ALPHA KETOESTER DERIVATIVE; COPPER COMPLEX; ESTER DERIVATIVE; HETEROARYLIDENE TETHERED BIS(OXAZOLINE) COPPER COMPLEX; INDOLE DERIVATIVE; PYRROLE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION;

EID: 84865275795     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc34803a     Document Type: Article

References (37)

1. T. B Poulsen, K. A. Jørgensen, Chem. Rev., 2008, 108, 2903
2. S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev., 2009, 38, 2190
3. M. Bandini, A. Eichholzer, Angew. Chem., 2009, 121, 9786
4. Angew. Chem., Int. Ed., 2009, 48, 9608
5. M. Bandini and A. Umani-Ronchi, Catalytic Asymmetric Friedel-Crafts Alkylations, Wiley-VCH, Weinheim, 2009
6. M. Zeng, S.-L. You, Synlett, 2010, 1289
7. V. Terrasson, R. M de Figueiredo, J. M Campagne, Eur. J. Org. Chem., 2010, 2635
8. L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia, H. Huang, Chem. Eur. J., 2010, 16, 1638
9. W. Wang, X. Liu, W. Cao, J. Wang, L. Lin, X. Feng, Chem. Eur. J., 2010, 16, 1664
10. D. Enders, C. Wang, M. Mukanova, A. Greb, Chem. Commun., 2010, 46, 2447
11. P. Bachu, T. Akiyama, Chem. Commun., 2010, 4112
12. H. Y. Kim, S. Kim, K. Oh, Angew. Chem., Int. Ed., 2010, 49, 4476
13. G. Blay, I. Fernández, M. C. Muñoz, J. R. Pedro, C. Vila, Chem. Eur. J., 2010, 16, 9117
14. F.-X. Xu, D. Huang, H. Chao, W. Shen, X.-F. Lin, Y.-G. Wang, J. Org. Chem., 2010, 75, 8677
15. L. Wen, Q. Shen, X. Wan, L. Lu, J. Org. Chem., 2011, 76, 2282
16. L.-Y. Chen, H. He, W.-H. Chan, A. W. M. Lee, J. Org. Chem., 2011, 76, 7141
17. C.-H. Xing, Y.-X. Liao, J. Ng, Q.-S. Hu, J. Org. Chem., 2011, 76, 4125
18. A. Rahman, A. Basha and Indole Alkaloids, Harwood Academic Publishers, Amsterdam, 1998
19. M. Bandini, A. Eichholzer, Angew. Chem., Int. Ed., 2009, 48, 9608
20. Heterocycles in Natural Product Synthesis, ed. K. C. Majumdar and S. K. Chattopadhyay, Wiley-VCH, Weinheim, 2011
21. C. C. J. Loh, D. Enders, Angew. Chem., Int. Ed., 2012, 51, 46
22. K. B Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem., Int. Ed., 2001, 40, 160
23. G. Desimoni, G. Faita, M. Toscanini, M. Boiocchi, Chem. Eur. J., 2008, 14, 3630
24. Y. Liu, D. Shang, X. Zhou, Y. Zhu, L. Lin, X. Liu, X. Feng, Org. Lett., 2010, 12, 180
25. J. Lv, X. Li, L. Zhong, S. Z. Luo, J.-P. Cheng, Org. Lett., 2010, 12, 1096
26. Y.-J. Sun, N. Li, Zh.-B. Zheng, L. Liu, Y.-B. Yu, Zh.-H. Qin, B. Fu, Adv. Synth. Catal., 2009, 351, 3113
27. I. W. Davies, L. Gerena, L. Castonguay, C. H. Senanayake, R. D. Larsen, T. R. Verhoeven, P. J Reider, Chem. Commun., 1996, 1753
28. I. W. Davies, R. J. Deeth, R. D. Larsen, P. J. Reider, Tetrahedron Lett., 1999, 40, 1233
29. S. E Denmark, C. M. Stiff, J. Org. Chem., 2000, 65, 5875
30. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc., 2007, 129, 10029
31. B. M. Trost, C. Müller, J. Am. Chem. Soc., 2008, 130, 2438
32. H. Liu, S.-F. Lu, J. Xu, D.-M. Du, Chem. Asian J., 2008, 3, 1111
33. N. Yokoyama, T. Arai, Chem. Commun., 2009, 3285
34. Y.-F. Sheng, Q. Gu, A.-J. Zhang, S.-L. You, J. Org. Chem., 2009, 74, 6899
35. P. K. Singh, V. K. Singh, Org. Lett., 2010, 12, 80
36. M. Johannsen, K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757
37. G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev., 2006, 106, 3561