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Chiral Bis(Oxazolinyl)thiophenes for Enantioselective Cu(II)-Catalyzed Friedel–Crafts Alkylation of Indole Derivatives with Nitroalkenes

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Abstract

A series of chiral bis(oxazoline)thiophenes were used as chiral ligands in the Cu(II)-catalyzed asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes, and the effects of reaction conditions on the yield and enantioselectivity were investigated. The ligand 1c was identified as the best ligand of this family in the same reaction.

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References

  1. Sundberg RJ (1970) In: The chemistry of indoles. Academic Press, New York

    Google Scholar 

  2. Brown RK (1972) In: Houlihan WJ (ed) Indoles. Wiley-Interscience, New York

    Google Scholar 

  3. Herrea RP, Sgarzani V, Bernardi VL, Ricci A (2005) Angew Chem Int Ed 44:6576

    Article  Google Scholar 

  4. Gaunt MJ, Johansson CCC, McNally A, Vo NT (2007) Drug Discovery Today 12:8

    Article  CAS  Google Scholar 

  5. Poulsen TB, Jørgensen KA (2008) Chem Rev 108:2903

    Article  CAS  Google Scholar 

  6. Ganesh M, Seidel D (2008) J Am Chem Soc 130:16464

    Article  CAS  Google Scholar 

  7. Scettri A, Villano R, Acocella MR (2009) Molecules 14:3030

    Article  CAS  Google Scholar 

  8. Terada M (2010) Synthesis 12:1929

    Article  Google Scholar 

  9. Sakamoto T, Itoh J, Mori K, Akiyama T (2010) Org Biomol Chem 8:5448

    Article  CAS  Google Scholar 

  10. Rueping M, Nachtsheim BJ (2010) Beilstein J Org Chem 6:1

    Article  Google Scholar 

  11. Kim HY, Kim S, Oh K (2010) Angew Chem Int Ed 49:1

    Article  Google Scholar 

  12. Liu H, Du DM (2010) Adv Synth Catal 352:1113

    Article  CAS  Google Scholar 

  13. Guo FF, Lia GY, Xiong SS, Wang SJ, Wang ZY (2010) Chem Eur J 16:6433

    Google Scholar 

  14. Arai T, Awata A, Wasai M, Yokoyama N, Masu H (2011) J Org Chem 76:5450

    Article  CAS  Google Scholar 

  15. Lin S, Jacobsen EN (2012) Nat Chem 4:817

    Article  CAS  Google Scholar 

  16. Chauhan P, Chimni SS (2012) R Soc Chem Adv 2:6117

    CAS  Google Scholar 

  17. Chen LY, Guillarme S, Saluzzo C (2013) Arkivoc 3:227

    Google Scholar 

  18. You SL, Cai Q, Zeng M (2009) Chem Soc Rev 38:2190

    Article  CAS  Google Scholar 

  19. Lin SZ, You TP (2009) Tetrahedron 65:1010

    Article  CAS  Google Scholar 

  20. Wu LY, Hao XQ, Xu YX, Jia MQ, Wang TN, Gong JF, Song MP (2009) Organometallics 28:3369

    Article  CAS  Google Scholar 

  21. McKeon SC, Müller-Bunz H, Guiry PJ (2009) Eur J Org Chem 2009:4833

    Article  Google Scholar 

  22. Yokoyama N, Arai T (2009) Chem Commun 22:3285

    Article  Google Scholar 

  23. Kim HY, Kim S, Oh K (2010) Angew Chem Int Ed 49:4476

    Article  CAS  Google Scholar 

  24. Terrasson V, De Figueiredo RM, Campagne JM (2010) Eur J Org Chem 2010:2635

    Article  Google Scholar 

  25. Zeng M, You SL (2010) Synlett 9:1289

    Google Scholar 

  26. Wu J, Li X, Wu F, Wan B (2011) Org Lett 13:4834

    Article  CAS  Google Scholar 

  27. McKeon SC, Müller-Bunz H, Guiry PJ (2011) Eur J Org Chem 2011:7107

    Article  CAS  Google Scholar 

  28. Hao XQ, Xu YX, Yang MJ, Wang L, Niu JL, Gong JF, Song MP (2012) Organometallics 31:835

    Article  CAS  Google Scholar 

  29. Chen LA, Tang X, Xi J, Xu W, Gong L, Meggers E (2013) Angew Chem Int Ed 52:14021

    Article  CAS  Google Scholar 

  30. Liu H, Lu SF, Xu J, Du DM (2008) Chem Asian J 3:1111

    Article  CAS  Google Scholar 

  31. Liu H, Du DM (2010) Eur J Org Chem 2010:2121

    Article  Google Scholar 

  32. Peng J, Du DM (2012) Eur J Org Chem 2012:4042

    Article  CAS  Google Scholar 

  33. Gao JR, Wu H, Xiang B, Yu WB, Han L, Jia YX (2013) J Am Chem Soc 135:2983

    Article  CAS  Google Scholar 

  34. Jia YX, Zhu SF, Yang Y, Zhou QL (2006) J Org Chem 71:75

    Article  CAS  Google Scholar 

  35. Lu SF, Du DM, Xu J (2006) Org Lett 8:2115

    Article  CAS  Google Scholar 

  36. Hargaden GC, Guiry PJ (2009) Chem Rev 109:2505

    Article  CAS  Google Scholar 

  37. Desimoni G, Faita G, Jørgensen A (2011) Chem Rev 111:PR284

    Article  CAS  Google Scholar 

  38. Gao MZ, Kong DY, Clearfied A, Zingaro RA (2004) Tetrahedron Lett 45:5649

    Article  CAS  Google Scholar 

  39. Li WJ, Qiu SX (2010) J Heterocycl Chem 47:1340

    Article  CAS  Google Scholar 

Download references

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Correspondence to Weijie Li.

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Li, W. Chiral Bis(Oxazolinyl)thiophenes for Enantioselective Cu(II)-Catalyzed Friedel–Crafts Alkylation of Indole Derivatives with Nitroalkenes. Catal Lett 144, 943–948 (2014). https://doi.org/10.1007/s10562-014-1228-2

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  • DOI: https://doi.org/10.1007/s10562-014-1228-2

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