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Part of the book series: Springer Theses ((Springer Theses))

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Abstract

The recent developments of the organocatalytic asymmetric reactions are summarized in this chapter. Among them, the hydrogen bond (HB) donor catalysts such as thiourea catalysts are well known as effective organocatalyst motif. My research group has developed the thiourea catalyst bearing a tertiary amino group. In the concept of this catalyst, the thiourea moiety and the tertiary amino group act as a Brønsted acid and a Brønsted base, respectively. These motifs activate both the electrophiles and the nucleophiles, respectively, resulting in a considerable acceleration of the reaction rate. So far, a number of other groups including our own have reported a variety of asymmetric reactions by using this concept. Recently, based on this concept, various bifunctional organocatalysts having other HB donor moieties than thiourea or possessing different functional groups than basic amino group have been developed.

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References

  1. Nemoto T, Hamada Y (2011) Tetrahedron 67:667

    Article  CAS  Google Scholar 

  2. Zhou F, Liu Y-L, Zhoua J (2010) Adv Synth Catal 352:1381

    Article  CAS  Google Scholar 

  3. NĂ¡jera C, Sansano JM (2007) Chem Rev 107:4584

    Article  Google Scholar 

  4. Ma J-A, Cahard D (2004) Angew Chem Int Ed 43:4566

    Article  CAS  Google Scholar 

  5. List B, Lerner RA, Barbas CF III (2000) J Am Chem Soc 122:2395

    Article  CAS  Google Scholar 

  6. Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138

    Article  CAS  Google Scholar 

  7. Berkessel A, Gröger H (2005) Asymmetric organocatalysis. Wiley-VCH, Weinheim

    Book  Google Scholar 

  8. Ooi T, Kameda M, Maruoka K (1999) J Am Chem Soc 121:6519

    Article  CAS  Google Scholar 

  9. Corey EJ, Noe MC, Xu F (1998) Tetrahedron Lett 39:5347

    Article  CAS  Google Scholar 

  10. Uraguchi D, Terada M (2004) J Am Chem Soc 126:5356

    Article  CAS  Google Scholar 

  11. Akiyama T, Itoh J, Yokota K, Fuchibe K (2004) Angew Chem Int Ed 43:1566

    Article  CAS  Google Scholar 

  12. Nakashima D, Yamamoto H (2006) J Am Chem Soc 128:9626

    Article  CAS  Google Scholar 

  13. Torii H, Nakadai M, Ishihara K, Saito S, Yamamoto H (1983) Angew Chem Int Ed 2004:43

    Google Scholar 

  14. Tang Z, Yang Z-H, Cheng X-H, Cun L-F, Mi A-Q, Jiang Y-Z, Gong L-Z (2005) J Am Chem Soc 127:9285

    Article  CAS  Google Scholar 

  15. Hayashi Y, Itoh T, Aratake S, Ishikawa H (2008) Angew Chem Int Ed 47:2082

    Article  CAS  Google Scholar 

  16. Kawabata T, Muramatsu W, Nishio T, Shibata T, Schedel H (2007) J Am Chem Soc 129:12890

    Article  CAS  Google Scholar 

  17. Wenzel AG, Jacobsen EN (2002) J Am Chem Soc 124:12964

    Article  CAS  Google Scholar 

  18. Ye W, Jiang Z, Zhao Y, Goh SLM, Leow D, Soh Y-T, Tan C-H (2007) Adv Synth Catal 349:2454

    Article  CAS  Google Scholar 

  19. Kita T, Georgieva A, Hasimoto Y, Nakata T, Nagasawa K (2002) Angew Chem Int Ed 41:2832

    Article  CAS  Google Scholar 

  20. Takikawa H, Suzuki K (2007) Org Lett 9:2713

    Article  CAS  Google Scholar 

  21. Mennen SM, Gipson JD, Kim YR, Miller SJ (2005) J Am Chem Soc 127:1654

    Article  CAS  Google Scholar 

  22. Matsui K, Takizawa H, Sasai H (2005) J Am Chem Soc 127:3680

    Article  CAS  Google Scholar 

  23. Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713

    Article  CAS  Google Scholar 

  24. Schreiner PR (2003) Chem Soc Rev 22:289

    Article  Google Scholar 

  25. Takemoto Y (2005) Org Biomol Chem 3:4299

    Article  CAS  Google Scholar 

  26. Taylor MS, Jacobsen EN (2006) Angew Chem Int Ed 45:1520

    Article  CAS  Google Scholar 

  27. Okino T, Hoashi Y, Takemoto Y (2003) J Am Chem Soc 125:12672

    Article  CAS  Google Scholar 

  28. Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y (2005) J Am Chem Soc 127:119

    Article  CAS  Google Scholar 

  29. Okino T, Nakamura S, Furukawa T, Takemoto Y (2004) Org Lett 6:625

    Article  CAS  Google Scholar 

  30. Xu X, Furukawa T, Okino T, Miyabe H, Takemoto Y (2006) Chem Eur J 12:466

    Article  Google Scholar 

  31. Xie J, Yoshida K, Takasu K, Takemoto Y (2008) Tetrahedron Lett 49:6910

    Article  CAS  Google Scholar 

  32. Xu X, Yabuta T, Yuan P, Takemoto Y (2006) Synlett 137

    Google Scholar 

  33. Kimmel KL, Robak MT, Ellman JA (2009) J Am Chem Soc 131:8754

    Article  CAS  Google Scholar 

  34. Malerich JP, Hagihara K, Rawal VH (2008) J Am Chem Soc 130:14416

    Article  CAS  Google Scholar 

  35. AlmaÅŸi D, Alonso DA, GĂ³mez-Bengoa E, NĂ¡jera C (2009) J Org Chem 74:6163

    Article  Google Scholar 

  36. Zhang L, Lee M-M, Lee S-M, Lee J, Cheng M, Jeong B-S, Park H-G, Jewb S-S (2009) Adv Synth Catal 351:3063

    Article  CAS  Google Scholar 

  37. Tan KL, Jacobsen EN (2007) Angew Chem Int Ed 46:1315

    Article  CAS  Google Scholar 

  38. Herrera RP, Sgarzani V, Bernardi L, Ricci A (2005) Angew Chem Int Ed 44:6576

    Article  CAS  Google Scholar 

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Correspondence to Tsubasa Inokuma .

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Inokuma, T. (2013). Introduction. In: Development of Novel Hydrogen-Bond Donor Catalysts. Springer Theses. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54231-5_1

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