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Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media

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Abstract

Chiral amphiphilic conjugate catalysts were designed and synthesized by covalently connecting l-proline with an inexpensive natural product, isosteviol. These catalysts demonstrated remarkable efficiency in the asymmetric α-aminoxylation of aldehydes and ketones using nitrosobenzene in phosphate buffer solution, resulting in good to high yields and excellent enantioselectivities without using any additives. At pH 9.1, the amphiphilic catalysts showed a pH responsive ability in phosphate buffer solution, which facilitated the excellent O-selectivity reactions, illustrating a viable approach for the development of asymmetric supra-molecular catalysts.

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References

  1. Davis FA, Chen BC (1995) Methods of organic chemistry. Houben–Weyl Thieme, Stuttgart

    Google Scholar 

  2. Enders D, Reinhold U (1994) Synlett 10:792

    Article  Google Scholar 

  3. Cho BT, Chun YS (1998) J Org Chem 63:5280

    Article  CAS  Google Scholar 

  4. Cho BT, Chun YS (1999) Tetrahedron Asymmetr 10:1843

    Article  CAS  Google Scholar 

  5. Davis FA, Chen BC (1992) Chem Rev 92:919

    Article  CAS  Google Scholar 

  6. Momiyama N, Yamamoto H (2003) J Am Chem Soc 125:6038

    Article  CAS  Google Scholar 

  7. Zhong G (2003) Angew Chem Int Ed 42:4247

    Article  CAS  Google Scholar 

  8. Brown SP, Brochu MP, Sinz CJ, MacMillan DWC (2003) J Am Chem Soc 125:10808

    Article  CAS  Google Scholar 

  9. Hayashi Y, Yamaguchi J, Hibino K, Shoji M (2003) Tetrahedron Lett 44:8293

    Article  CAS  Google Scholar 

  10. Hayashi Y, Yamaguchi J, Sumiya T, Shoji M (2004) Angew Chem Int Ed 43:1112

    Article  CAS  Google Scholar 

  11. Bøgevig A, Sundén H, Córdova A (2004) Angew Chem Int Ed 43:1109

    Article  Google Scholar 

  12. Córdova A, Sunden H, Bogevig A, Johansson M, Himo F (2004) Chem Eur J 10:3673

    Article  Google Scholar 

  13. Hayashi Y, Yamaguchi J, Hibino K, Sumiya T, Urushima T, Shoji M, Hashizume D, Koshino K (2004) Adv Synth Catal 346:1435

    Article  CAS  Google Scholar 

  14. Font D, Bastero A, Sayalero S, Jimeno C, Pericàs MA (2007) Org Lett 9:1943

    Article  CAS  Google Scholar 

  15. Mielgo A, Velilla I, Gómez-Bengoa E, Palomo C (2010) Eur J Org Chem 16:496

    Google Scholar 

  16. Wang W, Wang J, Lia H, Liao LX (2004) Tetrahedron Lett 45:7235

    Article  CAS  Google Scholar 

  17. Wang W, Wang J, Li H (2004) Tetrahedron Lett 45:7243

    Article  CAS  Google Scholar 

  18. Sundén H, Dahlin N, Ibrahem I, Adolfsson H, Córdova A (2005) Tetrahedron Lett 46:3385

    Article  Google Scholar 

  19. Jiao P, Kawasaki M, Yamamoto H (2009) Angew Chem Int Ed 48:3333

    Article  CAS  Google Scholar 

  20. Gruttadauria M, Salvo AMP, Giacalone F, Agrigento P, Noto R (2009) Eur J Org Chem 31:5437

    Article  Google Scholar 

  21. Alza E, Cambeiro XC, Jimeno C, Pericas MA (2007) Org Lett 9:3717

    Article  CAS  Google Scholar 

  22. Liu YX, Sun YN, Tan HH, Tao JC (2008) Catal Lett 120:281

    Article  CAS  Google Scholar 

  23. Liu YX, Sun YN, Tan HH, Liu W, Tao JC (2007) Tetrahedron Asymmetr 18:264

    Google Scholar 

  24. Gao JS, Liu J, Tang JY, Jiang DM, Li B, Yang QH (2010) Chem Eur J 16:7852

    Article  CAS  Google Scholar 

  25. Chua PJ, Tan B, Zhong GF (2009) Green Chem 11:543

    Article  CAS  Google Scholar 

  26. Yang L, Liu RH, Wang B, Weng LL, Zheng H (2009) Tetrahedron Lett 50:2628

    Article  CAS  Google Scholar 

  27. Font D, Jimeno C, Pericàs MA (2006) Org Lett 8:4653

    Article  CAS  Google Scholar 

  28. Font D, Sayalero S, Bastero A, Jimeno C, Pericàs MA (2008) Org Lett 10:337

    Article  CAS  Google Scholar 

  29. Dickerson TJ, Janda KD (2002) J Am Chem Soc 124:3220

    Article  CAS  Google Scholar 

  30. Córdova A, Notz W, Barbas CF III (2002) Chem Commun, p 3024

  31. Hu SS, Li JY, Xiang JF, Pan J, Luo SZ, Cheng JP (2010) J Am Chem Soc 132:7216

    Article  CAS  Google Scholar 

  32. Lin Y, Han X, Huang J, Fu H, Yu CJ (2009) Colloid Interface Sci 330:449

    Article  CAS  Google Scholar 

  33. Wu Y, Yang JH, Dai GF, Li CJ, Tian GQ, Ma WY, Tao JC (2009) Bioorgan Med Chem 17:1464

    Article  CAS  Google Scholar 

  34. Wu Y, Dai GF, Yang JH, Zhang YX, Zhu Y, Tao JC (2009) Bioorg Med Chem Lett 19:1818

    Article  CAS  Google Scholar 

  35. An YJ, Zhang YX, Wu Y, Liu ZM, Pi C, Tao JC (2010) Tetrahedron Asymmetr 21:688

    Article  CAS  Google Scholar 

  36. Hayashi Y, Aratake S, Okano T, Takahashi J, Sumiya T, Shoji M (2006) Angew Chem Int Ed 45:5527

    Article  CAS  Google Scholar 

  37. Fu YQ, An YJ, Liu WM, Li ZC, Zhang G, Tao JC (2008) Catal Lett 124:397

    Article  CAS  Google Scholar 

  38. Verma G, Aswal VK, Hassan P (2009) Soft Matter 5:2919

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors are thankful to the financial support of the Natural Science Foundation of China (NSFC 20772113).

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Authors and Affiliations

  1. Department of Chemistry, New Drug Research and Development Center, Zhengzhou University, 450052, Zhengzhou, People’s Republic of China

    Ya-Jie An, Chuan-Chuan Wang, Yuan-Zhen Xu, Wei-Juan Wang & Jing-Chao Tao

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  1. Ya-Jie An
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  2. Chuan-Chuan Wang
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  3. Yuan-Zhen Xu
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  4. Wei-Juan Wang
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  5. Jing-Chao Tao
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Correspondence to Jing-Chao Tao.

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An, YJ., Wang, CC., Xu, YZ. et al. Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media. Catal Lett 141, 1123–1129 (2011). https://doi.org/10.1007/s10562-011-0574-6

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