Highly enantioselective friedel-crafts reaction of indole with alkylidenemalonates catalyzed by heteroarylidene malonate-derived bis(oxazoline) copper(II) complexes

Advanced Synthesis and Catalysis

Volumn 351, Issue 18, 2009, Pages 3113-3117

  Sun, Yan Jin ^a   Li, Nan ^a   Zheng, Zhong Bo ^a   Liu, Lei ^a   Yu, Yan Bo ^a   Qin, Zhao Hai ^a   Fu, Bin ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Bis(oxazolines); Friedel crafts reaction; Heteroarylidenemalonates; Indoles

Indexed keywords

EID: 73349130739     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900669     Document Type: Article

References (56)

1. st edn, 1991, Vol. III, p293;
2. R. M. Roberts, A. A. Khalaf, Friedel-Crafts Alkylation Chemistry - A Century of Discovery, Dekker, New York, 1984;
3. G. A. Olah, Friedel-Crafts and Related Reactions, Wiley-Interscience, New York, 1964, Vol. II, part 1;
4. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett., 2005, 1199.
5. For selected examples, see: a) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
6. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. Angew. Chem. 2005, 117, 6734;
7. Angew. Chem. 2005, 117, 6734;
8. Angew. Chem. Int. Ed. 2005, 44, 6576;
9. K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jø-gensen, Angew. Chem. 2001, 113, 164;
10. Angew. Chem. Int. Ed. 2001, 40, 160;
11. H. Li, Y.-Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063;
12. Y. Q. Wang, J. Song, R. Hong, H. m. Li, L. Deng, J. Am. Chem. Soc. 2006, 128, 8156;
13. D. A. Evans, K. R. Fandrick, H.-J. Song, J. Am. Chem. Soc. 2005, 127, 8942;
14. Y.-X. Jia, S.-F. Zhu, Y. Yang, Q.-L. Zhou, J. Org. Chem. 2006, 71, 75;
15. S.-F. Lu, D.-M. Du, J. Xu, Org. Lett. 2006, 8, 2115;
16. H. Liu, S. F. Lu, J. X. Xu, D. M. Du, Chem. Asian J. 2008, 3, 1111;
17. Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484;
18. Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem. 2007, 119, 5661;
19. Angew. Chem. Int. Ed. 2007, 46, 5565;
20. A. J. Boersma, B. L. Feringa, G. Roelfes, Angew. Chem. 2009, 121, 3396;
21. Angew. Chem. Int. Ed. 2009, 48, 3346;
22. D. A. Evans, K. R. Fandrick, Org. Lett. 2006, 8, 2249;
23. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 129, 10029;
24. Q. Kang, X.-J. Zheng, S.-L. You, Chem. Eur. J. 2008, 14, 3539;
25. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. Eur. J. 2009, 15, 3351;
26. H. L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y. C. Chen, Angew. Chem. 2009, 121, 5847;
27. Angew. Chem. Int. Ed. 2009, 48, 5737.
28. a) J. Bosch, M.-L. Bennasar, Synlett., 1995, 587;
29. D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1;
30. S. E. O'Connor; J. J. Maresh, Nat. Prod. Rep. 2006, 23, 532;
31. M. Amat, N. Llor, J. Bosch, X. Solans, Tetrahedron 1997, 53, 719;
32. th edn., Georg Thieme Verlag, New York, 2001.
33. a) W. Zhuang, T. Hansen, K. A. Jørgensen, Chem. Commun. 2001, 347;
34. T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108. 2903.
35. a) J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030;
36. J. Zhou, M.-C. Ye, Z.-Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309;
37. J. Zhou, Y. Tang, Chem. Commun. 2004, 432;
38. J. Zhou, M.-C. Ye, Y. Tang, J. Comb. Chem. 2004, 6, 301;
39. M.-C. Ye, B. Li, J. Zhou, X.-L. Sun, Y. Tang, J. Org. Chem. 2005, 70, 6108.
40. a) R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Org. Lett. 2006, 8, 6099;
41. A. Schatz, R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Chem. Eur. J. 2008, 14, 7259.
42. Y.-I. Liu, D.-J. Shang, X. Zhou, X. H. Liu, X.-M. Feng, Chem. Eur. J. 2009, 15, 2055.
43. a) I. W. Davies, L. Gerena, L. Castonguay, C. H. Senanayake, R. D. Larsen, T. R. Verhoeven, P. J. Reider, Chem. Commun. 1996, 1753;
44. I. W. Davies, R. J. Deeth, R. D. Larsen, P. J. Reider, Tetrahedron Lett. 1999, 40, 1233.
45. S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875.
46. a) E. P. Carreiro, S. Chercheja; N. Moura, S. C. Gertrudes, A. J. Burke,. Inorg. Chem. Commun. 2006, 9, 823;
47. A. J. Burke, E. P. Carreiro, S. Chercheja, N. M. M. Moura, J. P. Ramalho, A. I. Rorigues, C. I. M. Santos, J. Organomet. Chem. 2007, 692, 4863. [11] a) D.-M. Du, B. Fu, W.-T. Hua, Tetrahedron 2003, 59, 1933;
48. S. E. Denmark, N. Nakajimn, O. J. Nicoise, A. M. Paucher, J. P. Edwards, J. Org. Chem. 1995, 60, 4884. [12] For the reversal of enantioselectivity just by changing solvents in catalysis, please see: a) J. Thorhauge, M. Roberson, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J, 2002, 8, 1888;
49. M. P. Sibi, M. Liu, Curr. Org. Chem. 2001, 5, 719;
50. G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, E. Giannini, Chem. Soc. Rev. 2003, 32, 115. [13] a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325;
51. R. Rasappan, D. Laventine, O. Reiser, Coord. Chem. Rev. 2008, 252, 702;
52. D. A. Evans, S. J. Miller, T. Lectka, P. von Matt, J. Am. Chem. Soc. 1999, 121, 7559;
53. D. A. Evans, T. Rovis, M. C. Kozlowski, C. W. Downey, J. S. Tedrow, J. Am. Chem. Soc. 2000, 122, 9134;
54. D. A. Evans, T. Rovis, M. C. Kozlowski, J. S. Tedrow, J. Am. Chem. Soc. 1999, 121 1994;
55. G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561;
56. T. B. Poulsen, K. A. Jøgensen, Chem. Rev. 2008, 108, 2903.