Highly enantioselective Friedel-Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes

Tetrahedron Asymmetry

Volumn 22, Issue 20-22, 2011, Pages 1874-1878

  Liu, Lei ^a   Zhao, Qiuying ^a   Du, Fengpei ^a   Chen, Hongliang ^a   Qin, Zhaohai ^a   Fu, Bin ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; HETEROARYLIDENE MALONATE TYPE BIS (OXAZOLINE); INDOLE DERIVATIVE; MALONIC ACID; N (INDOL 3 YL PHENYLMETHYL) 4 METHYLBENZENESULFONAMIDE; N [5 CHLORO INDOL 3 YL (4 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [5 METHOXY INDOL 3 YL (4 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [5 METHYL INDOL 3 YL (4 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [6 CHLORO INDOL 3 YL (4 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (2 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (3 BROMOPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (3 CYANPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (3 NITROPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (3 TRIFLUOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (4 BROMOPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (4 CHLOROPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (4 CYANPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (4 FLUOROPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N [INDOL 3 YL (4 NITROPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE 3A; N [INDOL 3 YL (4 TRIFLOROMETHYLPHENYL) METHYL] 4 METHYLBENZENESULFONAMIDE; N SULFONYL ALDIMINE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL;

EID: 82755198598     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.10.017     Document Type: Article

References (36)

1. For reviews on the Friedel-Crafts reaction, see: T.B. Poulsen, and K.A. Jøgensen Chem. Rev. 108 2008 2903
2. M. Bandini, and A. Umani-Ronchi Catalytic Asymmetric Friedel-Crafts Alkylation 2009 Wiley-VCH Weinheim, Germany p 1
3. M. Somei, and F. Yamada Nat. Prod. Rep. 21 2004 278 311
4. D.J. Faulkner Nat. Prod. Rep. 19 2002 1 48
5. R.J. Sundberg The Chemistry of Indoles 1996 Academic New York pp 105-118
6. For recent reviews on the asymmetric Friedel-Crafts reaction of indoles, see: R. Husmann, E. Sugiono, S. Mersmann, G. Raabe, M. Rueping, and C. Bolm Org. Lett. 13 2011 1044 1047
7. H.Y. Kim, S.-k. Kim, and K. Oh Angew. Chem., Int. Ed. 122 2010 4578 4580
8. Q. Cai, Z.-A. Zhao, and S.-L. You Angew. Chem., Int. Ed. 121 2009 7564 7567
9. Y.-L. Liu, D.-J. Shang, X. Zhou, X.-H. Liu, and X.-M. Feng Chem. Eur. J. 15 2009 2055 2058
10. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, and S.-L. You Chem. Eur. J. 15 2009 3351 3354
11. H.L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, and Y.C. Chen Angew. Chem. 121 2009 5847 5849 Angew. Chem., Int. Ed. 2009, 48, 5737-5739
12. T.B. Poulsen, and K.A. Jørgensen Chem. Rev. 108 2008 2903 2915
13. H. Liu, S.F. Lu, J.X. Xu, and D.M. Du Chem. Asian J. 3 2008 1111 1121
14. Q. Kang, X.-J. Zheng, and S.-L. You Chem. Eur. J. 14 2008 3539 3542
15. Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, and Q.-L. Zhou Angew. Chem. 119 2007 5661 5663 Angew. Chem., Int. Ed. 2007, 46, 5565-5567
16. D.A. Evans, K.R. Fandrick, H.-J. Song, K.A. Scheidt, and R. Xu J. Am. Chem. Soc. 129 2007 10029 10041
17. M. Johannsen Chem. Commun. 1999 2233 2234
18. Y. Jia, J. Xie, H. Duan, L. Wang, and Q. Zhou Org. Lett. 8 2006 1621 1624
19. Y. Wang, J. Song, R. Hong, H. Li, and L. Deng J. Am. Chem. Soc. 128 2006 8156 8157
20. Q. Kang, Z.-A. Zhao, and S.-L. You J. Am. Chem. Soc. 129 2007 1484 1485
21. B.-L. Wang, N.-K. Li, J.-X. Zhang, G.-G. Liu, T. Liu, Q. Shen, and X.-W. Wang Org. Biomol. Chem. 9 2011 2614 2617
22. G.C. Hargaden, and P.J. Guiry Chem. Rev. 109 2009 2505 2550
23. G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 106 2006 3561 3651
24. H.A. Mcmanus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
25. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325 335
26. A.K. Ghosh, P. Mathivannan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1 45
27. Recent literatures regarding bis(oxazoline) ligands: N. Merle, K.W. Törnroos, V. Jensen, and R.E. Le Roux J. Organomet. Chem. 696 2011 1691 1697
28. K. Lang, J.w. Park, and S. Hong J. Org. Chem. 75 2010 6424 6435
29. D. Frain, F. Kirby, P. McArdle, and P. O'Leary Tetrahedron Lett. 51 2010 4103 4106
30. X. Du, H. Liu, and D.-M. Du Tetrahedron: Asymmetry 21 2010 241 246
31. P.K. Singh, and V.K. Singh Org. Lett. 12 2010 80 83
32. G. Desimoni, G. Faita, M. Toscanini, and M. Boiocchi Chem. Eur. J. 15 2009 9674 9677
33. (g) Lin, Sh. -zh.; You, T. -p. Tetrahedron 2009, 65, 1010-1016
34. X. Cattoën, and M.A. Pericás Tetrahedron 65 2009 8199 8205
35. P.K. Singh, and V.K. Singh Org. Lett. 10 2008 4121 4124
36. Y.-J. Sun, N. Li, Z.B. Zheng, L. Liu, Y.-B. Yu, Z.-H. Qin, and B. Fu Adv. Synth. Catal. 351 2009 3113 3117