Asymmetric aza-Friedel-Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

Tetrahedron

Volumn 68, Issue 24, 2012, Pages 4830-4837

  Yang, Haohao ^a   Cui, Bing ^a   Wu, Guiping ^a   Miao, Zhiwei ^a,b   Chen, Ruyu ^a  

^a NANKAI UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; aza Friedel Crafts reaction; Carbohydrate auxiliaries; Indole; Lewis acid catalyzed

Indexed keywords

GALACTOSE; GALACTOSYLAMINE; INDOLE DERIVATIVE; METHYLAMINE; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; DIASTEREOISOMER; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84861225874     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.115     Document Type: Article

References (52)

1. J.A. Joule Indole and its Derivatives E.J. Thomas, Science of Synthesis (Houben-Weyl Methods of Molecular Transformations) Vol. 10 2000 Thieme Stuttgart Chapter 10.13
2. M. Bandini, A. Melloni, and F. Piccinelli G. Dyker, Handbooks of C-H Bonds Transformations Vol. 1 2005 Wiley-VCH Weinheim 150 157
3. K.A. Jorgensen Synthesis 2003 1117 1125
4. T.B. Poulsen, and K.A. Jorgensen Chem. Rev. 108 2008 2903 2915
5. Y.-F. Sheng, A.-J. Zhang, X.-J. Zheng, and S.-L. You Chin. J. Org. Chem. 28 2008 605 616
6. R.J. Sundberg The Chemistry of Indoles 1996 Academic New York, NY p 113
7. A. Aygun, and U. Pindur Curr. Med. Chem. 10 2003 1113 1127
8. M. Somei, and F. Yamada Nat. Prod. Rep. 22 2005 73 103
9. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748 8758
10. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209 2219
11. H. Lin, and S.J. Danishefsky Angew. Chem., Int. Ed. 42 2003 36 51
12. B.S. Jensen CNS Drug Rev. 8 2002 353 360
13. J.F.M. da Silva, S.J. Garden, and A.C. Pinto J. Braz. Chem. Soc. 12 2001 273 324
14. S. Bovens, A.S. Elfringhoff, M. Kaptur, D. Reinhardt, M. Schafers, and M. Lehr J. Med. Chem. 53 2010 8298 8308
15. G. Bartoli, G. Bencivenni, and R. Dalpozzo Chem. Soc. Rev. 39 2010 4449 4465
16. M. Bandini, and A. Eichholzer Angew. Chem., Int. Ed. 48 2009 9608 9644
17. J. Barluenga, F. Rodriguez, and F.J. Fananas Chem.-Asian J. 4 2009 1036 1048
18. K. Kruger, A. Tillack, and M. Beller Adv. Synth. Catal. 350 2008 2153 2167
19. M.A. Metwally, S. Shaaban, B.F. Abdel-Wahab, and G.A. El-Hiti Curr. Org. Chem. 13 2009 1475 1496
20. M. Bandini, A. Melloni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 550 556
21. K.A. Jorgensen Synthesis 2003 1117 1125
22. M. Bandini, and A. Umani-Ronchi Catalytic Asymmetric Friedel-Crafts Alkylations 2009 Wiley-WCH Verlag GmbH & Co. KGaA, Weinheim
23. Q. Kang, Z.-A. Zhao, and S.-L. You J. Am. Chem. Soc. 129 2007 1484 1485
24. Y.-X. Jia, J.-H. Xie, H.-F. Duan, L.-X. Wang, and Q.-L. Zhou Org. Lett. 8 2006 1621 1624
25. M. Johannsen Chem. Commun. 1999 2233 2234
26. S. Shirakawa, R. Berger, and J.L. Leighton J. Am. Chem. Soc. 127 2005 2858 2859
27. Q. Kang, Z.-A. Zhao, and S.-L. You Tetrahedron 65 2009 1603 1607
28. M.J. Wanner, P. Hauwert, H.E. Schoemaker, R. De Gelder, J.H. Van Maarseveen, and H. Hiemstra Eur. J. Org. Chem. 2008 180 185
29. A. Janczuk, W. Zhang, W.H. Xie, S.Z. Lou, J.-P. Cheng, and P.G. Wang Tetrahedron Lett. 43 2002 4271 4274
30. B. Jiang, C.-G. Yang, and X.-H. Gu Tetrahedron Lett. 42 2001 2545 2547
31. F. Lei, Y.-J. Chen, Y. Sui, L. Liu, and D. Wang Synlett 2003 1160 1164
32. B. Jiang, and Z.-G. Huang Synthesis 2005 2198 2204
33. M. Abid, L. Teixeira, and B. Török Org. Lett. 10 2008 933 935
34. T. Andreassen, L.-K. Hansen, and O.R. Gautun Eur. J. Org. Chem. 2008 4871 4876
35. B.-Y. Li, Z.-J. Li, and X.-B. Meng Carbohydr. Res. 345 2010 1708 1712
36. G.-W. Zhang, L. Wang, J. Nie, and J.-A. Ma Adv. Synth. Catal. 350 2008 1457 1463
37. D.E. Levy, and P. Fügedi The Organic Chemistry of Sugars 2006 Taylor and Francis Boca Raton, FL Chapter 11-16, pp 490-845
38. R. Katritzky, T. Narindoshvili, B. Draghici, and P. Angrish J. Org. Chem. 73 2008 511 516
39. S. Knauer, B. Kranke, L. Krause, and H. Kunz Curr. Org. Chem. 8 2004 1739 1761
40. M. Weymann, M. Scultz-Kukula, and H. Kunz Tetrahedron Lett. 39 1998 7835 7838
41. G. Zhou, W. Zheng, D. Wang, P. Zhang, and Y. Pan Helv. Chim. Acta 89 2006 520 526
42. H. Kunz, A. Burgard, and D. Schanzenbach Angew. Chem., Int. Ed. 36 1997 386 387
43. H. Kunz, and W. Sager Angew. Chem., Int. Ed. Engl. 26 1987 557 559
44. H. Kunz, and W. Pfrengle J. Am. Chem. Soc. 110 1988 651 652
45. H. Kunz, and W. Pfrengle Tetrahedron 44 1988 5487 5494
46. H. Kunz, and D. Schanzenbach Angew. Chem., Int. Ed. Engl. 28 1989 1068 1069
47. W. Pfrengle, and H. Kunz Angew. Chem., Int. Ed. Engl. 28 1989 1067 1068
48. W. Pfrengle, and H. Kunz J. Org. Chem. 54 1989 4261 4263
49. Y.-D. Wang, Y.-Y. Wang, J.-P. Yu, Z.-W. Miao, and R.-Y. Chen Chem. - Eur. J. 15 2009 9290 9293
50. H. Kunz, W. Sager, D. Schanzenbach, and M. Decker Liebigs Ann. Chem. 1991 649 654
51. I. Alonso, J. Esquivias, R. Gómez-Arrayás, and J.C. Carretero J. Org. Chem. 73 2008 6401 6404
52. H. Kunz, and K. Rück Angew. Chem., Int. Ed. Engl. 32 1993 336 358