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Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols

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Abstract

A series of novel chiral β-amino alcohols 3–5 and 7–10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34–48 % ee). The ee values of the desired 3-aryloxy-1,2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.

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References

  1. Terada M, Machioka K, Sorimachi K (2006) Angew Chem Int Ed 45:2254

    Article  CAS  Google Scholar 

  2. Saito S, Yamamoto H (2004) Acc Chem Res 37:570–579

    Article  CAS  Google Scholar 

  3. Akiyama T (2007) Chem Rev 107:5744

    Article  CAS  Google Scholar 

  4. Cobb AJ, Marson CM (2005) Tetrahedron 61:1269

    Article  CAS  Google Scholar 

  5. Forrat VJ, Ramón DJ, Yus M (2008) Tetrahedron Asymmetry 19:537

    Article  CAS  Google Scholar 

  6. Micheau JC, Buhse T, Lavabre D, Islas JR (2008) Tetrahedron Asymmetry 19:416

    Article  CAS  Google Scholar 

  7. Zhong J, Guo H, Wang M, Yin M, Wang M (2007) Tetrahedron Asymmetry 18:734

    Article  CAS  Google Scholar 

  8. Parambadath S, Singh AP (2009) Catal Today 141:161

    Article  CAS  Google Scholar 

  9. Xiaofeng W, Xiaohong L, Matthew MC, Ourida S, Jianliang X (2006) J Mol Catal A 247:153

    Article  Google Scholar 

  10. Zhou Y, Wang YW, Dou W, Zhang D, Lio WS (2009) Chirality 21:657

    Article  CAS  Google Scholar 

  11. Zhang YX, Du DM, Chen X, Lü SF, Hua WT (2004) Tetrahedron Asymmetry 15:177

    Article  Google Scholar 

  12. Chen YJ, Chen C (2007) Tetrahedron Asymmetry 18:1313

    Article  CAS  Google Scholar 

  13. Tschöp A, Marx A, Sreekanth AR, Schneider C (2007) Eur J Org Chem 14:2318

    Article  Google Scholar 

  14. Russo A, Lattanzi A (2008) Eur J Org Chem 16:2767

    Article  Google Scholar 

  15. Luo ZB, Hou XL, Dai LX (2007) Tetrahedron Asymmetry 18:443

    Article  CAS  Google Scholar 

  16. Wang Z, Sun X, Ye S, Wang W, Wang B, Wu J (2008) Tetrahedron Asymmetry 19:964

    Article  Google Scholar 

  17. Kumar P, Naidu V, Gupta P (2007) Tetrahedron 63:2745

    Article  CAS  Google Scholar 

  18. Lagos FM, Carballeira JD, Bermúdez JL, Alvarez E, Jose Sinisterra V (2004) Tetrahedron Asymmetry 15:763

    Article  Google Scholar 

  19. McKerlie F, Procter DJ, Wynne G (2002) Chem Commun 6:584

    Article  Google Scholar 

  20. Takahashi H, Sakuraba S, Takea H, Achiwa K (1990) J Am Chem Soc 112:5876

    Article  CAS  Google Scholar 

  21. Chen J, Shum W (1995) Tetrahedron Lett 36:2379

    Article  CAS  Google Scholar 

  22. Kitaori K, Furukawa Y, Yoshimoto H, Otera J (1999) Tetrahedron 55:14381

    Article  CAS  Google Scholar 

  23. Zhu X, Venkatasubbaiah K, Weck M, Lones CW (2010) J Mol Catal A 329:1

    Article  CAS  Google Scholar 

  24. Johnson RA, Sharplesss KB (1993) In: Ojima I (ed) Catalytic asymmetric synthesis. Wiley–VCH, New York, p 103

    Google Scholar 

  25. Jacobsen EN (1993) In Ojima I (ed) Catalytic asymmetric synthesis. Wiley–VCH, New York, p 287

    Google Scholar 

  26. Sun J, Yuan F, Yang M, Pan Y, Zhu C (2009) Tetrahedron Lett 50:548

    Article  CAS  Google Scholar 

  27. Kureshy RI, Kumar M, Agrawal S, Khan NH, Abdi SHR, Bajaj HC (2010) Tetrahedron Asymmetry 21:451

    Article  CAS  Google Scholar 

  28. Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN (1997) Science 277:936–938

    Article  CAS  Google Scholar 

  29. Bonollo S, Lanari D, Vaccaro L (2011) Eur J Org Chem 14:2587

    Article  Google Scholar 

  30. Ready JM, Jacobsen EN (1999) J Am Chem Soc 121:6086

    Article  CAS  Google Scholar 

  31. Peukert S, Jacobsen EN (1999) Org Lett 1:1245

    Article  CAS  Google Scholar 

  32. Groger H (2001) Adv Synth Catal 343:547

    Article  CAS  Google Scholar 

  33. Roberts SM (2001) J Chem Soc Perkin Transact 1:1475

    Article  Google Scholar 

  34. Reetz MT (2001) Angew Chem Int Ed 40:284

    Article  CAS  Google Scholar 

  35. Bala N, Chimni SS (2010) Tetrahedron Asymmetry 21:2879

    Article  CAS  Google Scholar 

  36. Turgut Y, Aral T, Karakaplan M, Deniz P, Hoşgören H (2010) Synth Commun 40:3365

    Article  CAS  Google Scholar 

  37. Panchgalle SP, Gore RG, Chavan SP, Kalkote UR (2009) Tetrahedron Asymmetry 20:1767

    Article  CAS  Google Scholar 

  38. Jonet A, Dassonville-Klimpt A, Da Nascimento S, Leger JM, Guillon J, Sonnet P (2011) Tetrahedron Asymmetry 22:138

    Article  CAS  Google Scholar 

  39. Wynberg H (1986) Top Stereochem 16:87–129

    Article  CAS  Google Scholar 

  40. Mucha P, Mlostron G, Jasinski M, Linden A, Heimgartner H (2008) Tetrahedron Asymmetry 19:1600

    Article  CAS  Google Scholar 

  41. Tye H, Eldred C, Wills M (2001) Tetrahedron Lett 43:155

    Article  Google Scholar 

Download references

Acknowledgments

We thank the Research Project Council of Dicle University (DÜBAP-08-FF-13) and the Scientific and Technological Research Council of Turkey (TUBİTAK) (Project no: 110T468) for their financial support.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey

    Mehmet Karakaplan & Halil Hoşgören

  2. Department of Chemistry, Faculty of Science and Art, University of Batman, Batman, Turkey

    Tarik Aral

Authors
  1. Tarik Aral
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  2. Mehmet Karakaplan
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  3. Halil Hoşgören
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Correspondence to Mehmet Karakaplan.

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Aral, T., Karakaplan, M. & Hoşgören, H. Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols. Catal Lett 142, 794–802 (2012). https://doi.org/10.1007/s10562-012-0814-4

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  • DOI: https://doi.org/10.1007/s10562-012-0814-4

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