Modification of pseudo-C3-symmetric trisoxazoline and its application to the Friedel-Crafts alkylation of indoles and pyrrole with alkylidene malonates

Synlett

Volumn , Issue 7, 2011, Pages 935-938

  Zhou, You Yun ^a   Sun, Xiu Li ^a   Zhu, Ben Hu ^a   Zheng, Jun Cheng ^a   Zhou, Jiao Long ^a   Tang, Yong ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

alkylation; asymmetric catalysis; copper; enantioselectivity; indoles

Indexed keywords

ALKYLIDENE MALONIC ACID DERIVATIVE; CUPRIC ION; INDOLE DERIVATIVE; MALONIC ACID DERIVATIVE; PYRROLE DERIVATIVE; TRISOXAZOLINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; SYNTHESIS;

EID: 79954622936     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259721     Document Type: Article

References (61)

1. For chiral trisoxazolines, see:, Hargaden G C., Guiry P J., Chem. Rev. 2009 109 2505
2. Gaab M, Bellemin-Laponnaz S, Gade L H., Chem. Eur. J. 2009 15 5450
3. Gade L H., Bellemin-Laponnaz S, Chem. Eur. J. 2008 14 4142
4. Foltz C, Stecker B, Marconi G, Bellemin-Laponnaz S, Wadepohl H, Gade L H., Chem. Eur. J. 2007 13 9912
5. Kim S.-G, Seong H R., Kim J, Ahn K H., Tetrahedron Lett. 2004 45 6835
6. Rocchetti M T., Fino V, Capriati V, Florio S, Luisi R, J. Org. Chem. 2003 68 1394
7. Bellemin-Laponnaz S, Gade L H., Angew. Chem. Int. Ed. 2002 41 3473
8. Capriati V, Florio S, Luisi R, Rocchetti M T., J. Org. Chem. 2002 67 759
9. Kim S.-G, Ahn K H., Tetrahedron Lett. 2001 42 4175
10. Kohmura Y, Katsuki T, Tetrahedron Lett. 2000 41 3941
11. Chuang T.-H, Fang J.-M, Bolm C, Synth. Commun. 2000 30 1627
12. Chan T H., Zheng G Z., Can. J. Chem. 1997 75 629
13. Kawasaki K, Katsuki T, Tetrahedron 1997 53 6337
14. Kawasaki K, Tsumura S, Katsuki T, Synlett 1995 1245
15. For achiral trisoxazolines, see:, Sorrell T N., Pigge F C., White P S., Inorg. Chim. Acta 1993 210 87
16. For selected recent reports on trisoxazolines in molecular recognition, see:, Kim J, Raman B, Ahn K H., J. Org. Chem. 2006 71 38
17. Kim J, Ryu D, Sei Y, Yamaguchi K, Ahn K H., Chem. Commun. 2006 1136
18. Kim J, Kim S G., Seong H R., Ahn K H., J. Org. Chem. 2005 70 7227
19. Kim S.-G, Kim K.-H, Kim Y K., Shin S K., Ahn K H., J. Am. Chem. Soc. 2003 125 13819
20. Ahn K H., Ku H.-Y, Kim Y, Kim S.-G, Kim Y K., Son H S., Ku J K., Org. Lett. 2003 5 1419
21. Kim S.-G, Kim K.-H, Jung J, Shin S K., Ahn K H., J. Am. Chem. Soc. 2002 124 591
22. Kim S.-G, Ahn K H., Chem. Eur. J. 2000 6 3399
23. Ahn K H., Kim S.-G, Jung J, Kim K.-H, Kim J, Chin J, Kim K, Chem. Lett. 2000 170
24. For reviews on chiral trisoxazoline in asymmetric catalysis, see ref. 1c and:, Hargaden G C., Guiry P J., Chem. Rev. 2009 109 2505
25. Desimoni G, Faita G, Jørgensen K A., Chem. Rev. 2006 106 3561
26. Zhou J, Tang Y, Chem. Soc. Rev. 2005 34 664
27. McManus H A., Guiry P J., Chem. Rev. 2004 104 4151
28. Ye M.-C, Li B, Zhou J, Sun X.-L, Tang Y, J. Org. Chem. 2005 70 6108
29. Zhou J, Ye M.-C, Huang Z.-Z, Tang Y, J. Org. Chem. 2004 69 1309
30. Zhou J, Ye M.-C, Tang Y, J. Comb. Chem. 2004 6 301
31. Zhou J, Tang Y, Chem. Commun. 2004 432
32. Zhou J, Tang Y, J. Am. Chem. Soc. 2002 124 9030
33. Kang Y.-B, Sun X.-L, Tang Y, Angew. Chem. Int. Ed. 2007 46 3918
34. Huang Z.-Z, Kang Y.-B, Zhou J, Ye M.-C, Tang Y, Org. Lett. 2004 6 1677
35. Zhou J, Tang Y, Org. Biomol. Chem. 2004 2 429
36. Ye M.-C, Li B, Zhou J, Sun X.-L, Tang Y, J. Org. Chem. 2005 70 6108
37. Ye M.-C, Zhou J, Huang Z.-Z, Tang Y, Chem. Commun. 2003 2554
38. Xu Z.-H, Zhu S.-N, Sun X.-L, Tang Y, Dai L.-X, Chem. Commun. 2007 1960
39. For recent reviews of catalytic asymmetric F-C reactions, see
40. Marques-Lopez E, Diez-Martinez A, Merino P, Herrera R P., Curr. Org. Chem. 2009 13 1585
41. You S.-L, Cai Q, Zeng M, Chem. Soc. Rev. 2009 38 2190
42. Poulsen T B., Jorgensen K A., Chem. Rev. 2008 108 2903
43. Rasappan R, Olbrich T, Reiser O, Adv. Synth. Catal 2009 351 1961
44. Zhou J.-L, Ye M.-C, Sun X.-L, Tang Y, Tetrahedron 2009 65 6877
45. Hui Y, Zhang Q, Jiang J, Lin L, Liu X, Feng X, J. Org. Chem. 2009 74 6878
46. Liu Y, Shang D, Zhou X, Liu X, Feng X, Chem. Eur. J. 2009 15 2055
47. Hong L, Wang L, Chen C, Zhang B, Wang R, Adv. Synth. Chem. 2009 351 772
48. Hong L, Wang L, Sun W, Wong K, Wang R, J. Org. Chem. 2009 74 6881
49. Kang Q, Zhao Z.-A, You S.-L, Tetrahedron 2009 65 1603
50. Chi Y G., Scroggins S T., Frechet J M. J., J. Am. Chem. Soc. 2008 130 6322
51. Schatz A, Rasappan R, Hager M, Gissibl A, Reiser O, Chem. Eur. J. 2008 14 7259
52. Liu H, Lu S.-F, Xu J, Du D.-M, Chem. Asian J. 2008 3 1111
53. Liu W.-B, He H, Dai L.-X, You S.-L, Org. Lett. 2008 10 1815
54. Lee S, MacMillan D W. C., J. Am. Chem. Soc. 2007 129 15438
55. Terada M, Sorimachi K, J. Am. Chem. Soc. 2007 129 292
56. Lakhdar S, Goumont R, Berionni G, Boubaker T, Kurbatov S, Terrier F, Chem. Eur. J. 2007 13 8317
57. Yang H, Hong Y.-T, Kim S, Org. Lett. 2007 9 2281
58. Blay G, Fernandez I, Pedro J R., Vila C, Org. Lett. 2007 9 2601
59. Dong H.-M, Lu H.-H, Lu L.-Q, Chen C.-B, Xiao W.-J, Adv. Synth. Catal. 2007 349 1597
60. Cornejo A, Fraile J M., García J I., Gil M J., Martínez-Merino V, Mayoral J A., Pires E, Villalba I, Synlett 2005 2321
61. Cao C.-L, Zhou Y.-Y, Sun X.-L, Tang Y, Tetrahedron 2008 64 10676