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Chiral Bicyclic Guanidine, Bis-Guanidinium, Pentanidium and Related Organocatalysts

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Guanidines as Reagents and Catalysts I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 50))

Abstract

The roles of chiral bicyclic guanidine, bis-guanidinium and pentanidium in catalysis are presented. Besides the usual Brønsted base reactivity, less known modes of interactions of these catalysts, such as Brønsted base–Brønsted acid and Brønsted–Lewis acid bifunctional activations will be discussed in this account. Pentanidiums are ‘super-guanidines’ with extended conjugation, and their roles in catalysis and halogen bonding will also be elaborated.

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Abbreviations

BARF:

[B[3,5-(CF3)2C6H3]4]−; Tetrakis(3,5-bis(trifluoromethyl)phenyl) borate

DBU:

1,8-Diazabicycloundec-7-ene

Eoc:

N-3-Ethylpentan-3-yloxycarbonyl

NHPI:

N-Hydroxyphthalimide

TBD:

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

TBO:

1,4,6-Triazabicyclo[3.3.0]oct-4-ene

References

  1. Palomo C, Oiarbide M, López R (2009) Chem Soc Rev 38:632

    Article  CAS  Google Scholar 

  2. Ishikawa T (ed) (2009) Superbases for organic synthesis. Wiley, Chichester

    Google Scholar 

  3. Schreiner PR (2003) Chem Soc Rev 32:289

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Takemoto Y (2010) Chem Pharm Bull 58:593

    Article  CAS  Google Scholar 

  6. Corey EJ, Ohtani M (1989) Tetrahedron Lett 30:5227

    Article  CAS  Google Scholar 

  7. Corey EJ, Grogan M (1999) Org Lett 1:157

    Article  CAS  Google Scholar 

  8. Coles MP (2009) Chem Commun 3659

    Google Scholar 

  9. Leow D, Tan C-H (2009) Chem Asian J 4:488

    Article  CAS  Google Scholar 

  10. Terada M (2010) J Synth Org Chem Jpn 68:1159

    Article  CAS  Google Scholar 

  11. Ishikawa T (2010) Chem Pharm Bull 58:1555

    Article  CAS  Google Scholar 

  12. Leow D, Tan CH (2010) Synlett 1589

    Google Scholar 

  13. Sohtome Y, Nagasawa K (2010) Synlett 1

    Google Scholar 

  14. Fu X, Tan C-H (2011) Chem Commun 47:8210

    Article  CAS  Google Scholar 

  15. Selig P (2013) Synthesis 45:703

    Article  CAS  Google Scholar 

  16. Echavarren E, Galan A, Lehn J-M, de Mendoza J (1989) J Am Chem Soc 109:4994

    Article  Google Scholar 

  17. Galán A, Andreu D, Echavarren AM, Prados P, de Mendoza J (1992) J Am Chem Soc 114:1511

    Article  Google Scholar 

  18. Gleich A, Schmidtchen FP, Mikulcik P, Müller G (1990) J Chem Soc Chem Commun 55

    Google Scholar 

  19. Davis AP, Dempsey KJ (1995) Tetrahedron Asymmetry 6:2829

    Article  CAS  Google Scholar 

  20. Howard-Jones A, Murphy PJ, Thomas DA (1999) J Org Chem 64:1039

    Article  CAS  Google Scholar 

  21. Allingham MT, Howard-Jones A, Murphy PJ, Thomas DA, Caulkett PWR (2003) Tetrahedron Lett 44:8677

    Article  CAS  Google Scholar 

  22. Ye W, Leow D, Goh SLM, Tan C-T, Chian C-H, Tan C-H (2006) Tetrahedron Lett 47:1007

    Article  CAS  Google Scholar 

  23. Wang C, Goh CMT, Xiao S, Ye W, Tan CH (2013) J Synth Org Chem Jpn 71:1145

    Article  CAS  Google Scholar 

  24. Ye W, Xu J, Tan C-T, Tan C-H (2005) Tetrahedron Lett 46:6875

    Article  CAS  Google Scholar 

  25. McKay AF, Kreling M-E (1962) Can J Chem 40:1160

    Article  CAS  Google Scholar 

  26. Kiesewetter MK, Scholten MD, Kirn N, Weber RL, Hedrick JL, Waymouth RM (2009) J Org Chem 74:9490

    Article  CAS  Google Scholar 

  27. 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 

  28. Jiang Z, Ye W, Yang Y, Tan C-H (2008) Adv Synth Catal 350:2345

    Article  CAS  Google Scholar 

  29. Wong MW, Ng AME (2014) Aust J Chem 67:1100

    Article  CAS  Google Scholar 

  30. Corey EJ (2002) Angew Chem Int Ed 41:1650

    Article  CAS  Google Scholar 

  31. Shen J, Tan CH (2008) Org Biomol Chem 6(18):3229

    Article  CAS  Google Scholar 

  32. Shen J, Nguyen TT, Goh Y-P, Ye W, Fu X, Xu J, Tan C-H (2006) J Am Chem Soc 128:13692

    Article  CAS  Google Scholar 

  33. Shen J, Tan CH (2008) Org Biomol Chem 6(22):4096

    Article  CAS  Google Scholar 

  34. Jiang Z, Zhang Y, Ye W, Tan C-H (2007) Tetrahedron Lett 48:51

    Article  CAS  Google Scholar 

  35. Fu X, Jiang Z, Tan CH (2007) Chem Commun 5058

    Google Scholar 

  36. Cho B, Tan C-H, Wong MW (2011) Org Biomol Chem 9:4550

    Article  CAS  Google Scholar 

  37. Leow D, Shen J, Su Y, Peh G (2014) Mini Rev Org Chem 11:410

    Article  CAS  Google Scholar 

  38. Thorat VH (2014) Synlett 25:1482

    Article  CAS  Google Scholar 

  39. Leow D, Lin S, Chittimalla SK, Fu X, Tan C-H (2008) Angew Chem Int Ed 47:5641

    Article  CAS  Google Scholar 

  40. Cho B, Tan C-H, Wong MW (2012) J Org Chem 77:6553

    Article  CAS  Google Scholar 

  41. Lin S, Leow D, Huang K-W, Tan C-H (2009) Chem Asian J 4:1741

    Article  CAS  Google Scholar 

  42. Leow D (2009) Chiral guanidine catalyzed enantioselective protonation reactions. Ph.D dissertation, National University of Singapore

    Google Scholar 

  43. Liu H, Leow D, Huang K-W, Tan C-H (2009) J Am Chem Soc 131:7212

    Article  CAS  Google Scholar 

  44. Liu H, Feng W, Kee C-W, Leow D, Loh W-T, Tan C-H (2010) Adv Synth Catal 352:3373

    Article  CAS  Google Scholar 

  45. Zhao Y, Lim X, Pan Y, Zong L, Feng W, Tan C-H, Huang K-W (2012) Chem Commun 48:5479

    Article  CAS  Google Scholar 

  46. Wang J, Liu H, Fan Y, Yang Y, Jiang Z, Tan C-H (2010) Chem Eur J 16:12534

    Article  CAS  Google Scholar 

  47. Wang J, Chen J, Kee CW, Tan C-H (2012) Angew Chem Int Ed 51:2382

    Article  CAS  Google Scholar 

  48. Jiang Z, Yang YY, Pan YH, Zhao YJ, Liu HJ, Tan C-H (2009) Chem Eur J 15:4925

    Article  CAS  Google Scholar 

  49. Jiang Z, Pan Y, Zhao Y, Ma T, Lee R, Yang Y, Huang K-W, Wong MW, Tan C-H (2009) Angew Chem Int Ed 48:3627

    Article  CAS  Google Scholar 

  50. Jing Z, Liu J, Chin KF, Chen W, Tan C-H, Jiang Z (2014) Aust J Chem 67:1119

    Article  CAS  Google Scholar 

  51. Pan Y, Zhao Y, Ma T, Yang Y, Liu H, Jiang Z, Tan C-H (2010) Chem Eur J 16:779

    Article  CAS  Google Scholar 

  52. Zhao Y, Pan Y, Liu H, Yang Y, Jiang Z, Tan C-H (2011) Chem Eur J 17:3571

    Article  CAS  Google Scholar 

  53. Zhao Y, Pan Y, Sim S-BD, Tan C-H (2012) Org Biomol Chem 10:479

    Article  CAS  Google Scholar 

  54. Pan Y, Tan CH (2011) Synthesis 2044

    Google Scholar 

  55. Pan Y, Kee CW, Jiang Z, Ma T, Zhao Y, Yang Y, Xue H, Tan CH (2011) Chem Eur J 17:8363

    Article  CAS  Google Scholar 

  56. Li L, Chen W, Yang W, Pan Y, Liu H, Tan C-H, Jiang Z (2012) Chem Commun 48:5124

    Article  CAS  Google Scholar 

  57. Yang C, Chen W, Yang W, Zhu B, Yan L, Tan C-H, Jiang Z (2013) Chem Asian J 8:2960

    Article  CAS  Google Scholar 

  58. Chen W, Yang W, Yan L, Tan C-H, Jiang Z (2013) Chem Commun 49:9854

    Article  CAS  Google Scholar 

  59. Ishikawa T, Araki Y, Kumamoto T, Seki H, Fukuda K, Isobe T (2001) Chem Commun 245

    Google Scholar 

  60. Sohtome Y, Hashimoto Y, Nagasawa K (2005) Adv Synth Catal 347:1643

    Article  CAS  Google Scholar 

  61. Terada M, Ube H, Yaguchi Y (2006) J Am Chem Soc 128:1454

    Article  CAS  Google Scholar 

  62. Uyeda C, Jacobsen EN (2008) J Am Chem Soc 130:9228

    Article  CAS  Google Scholar 

  63. Yu Z, Liu X, Zhou L, Lin L, Feng X (2009) Angew Chem Int Ed 48:5195

    Article  CAS  Google Scholar 

  64. Misaki T, Takimoto G, Sugimura T (2010) J Am Chem Soc 132:6286

    Article  CAS  Google Scholar 

  65. Zou L, Wang B, Mu H, Zhang H, Song Y, Qu J (2013) Org Lett 15:3106

    Article  CAS  Google Scholar 

  66. Zhang Y, Kee CW, Lee R, Fu X, Soh JYT, Loh EMF, Huang K-W, Tan C-H (2011) Chem Commun 47:3897

    Article  CAS  Google Scholar 

  67. Fu X, Loh W-T, Zhang Y, Chen T, Ma T, Liu H, Wang J, Tan C-H (2009) Angew Chem Int Ed 48:7387

    Article  CAS  Google Scholar 

  68. Dong S, Liu X, Chen X, Mei F, Zhang Y, Gao B, Lin L, Feng X (2010) J Am Chem Soc 132:10650

    Article  CAS  Google Scholar 

  69. Dong S, Liu X, Zhang Y, Lin L, Feng X (2011) Org Lett 13:5060

    Article  CAS  Google Scholar 

  70. Xiao X, Liu X, Dong S, Cai Y, Lin L, Feng X (2012) Chem Eur J 18:15922

    Article  CAS  Google Scholar 

  71. Dong S, Liu X, Zhu Y, He P, Lin L, Feng X (2013) J Am Chem Soc 135:10026

    Article  CAS  Google Scholar 

  72. Ma T, Fu X, Kee CW, Zong L, Pan Y, Huang K-W, Tan C-H (2011) J Am Chem Soc 133:2828

    Article  CAS  Google Scholar 

  73. Yang Y, Moinodeen F, Chin W, Ma T, Jiang Z, Tan C-H (2012) Org Lett 14:4762

    Article  CAS  Google Scholar 

  74. Zong L, Ban X, Kee CW, Tan C-H (2014) Angew Chem Int Ed 53:11849

    Article  CAS  Google Scholar 

  75. He W, Ge Y-C, Tan C-H (2014) Org Lett 16:3244

    Article  CAS  Google Scholar 

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Acknowledgements

We wish to thank our dedicated colleagues and collaborators whose names appeared in the citation list. This work is generously funded by National University of Singapore; Nanyang Technological University; Agency for Science, Technology and Research (A*STAR); and GlaxoSmithKline.

Author information

Authors and Affiliations

  1. Department of Chemistry, National Tsing Hua University, 101, Sec 2, Kuang-Fu Rd, Hsinchu, 30013, Taiwan, China

    Dasheng Leow

  2. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore

    Choon-Hong Tan

Authors
  1. Dasheng Leow
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  2. Choon-Hong Tan
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Corresponding author

Correspondence to Dasheng Leow .

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Editors and Affiliations

  1. Patheon Inc. , Linz, Austria

    Philipp Selig

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Leow, D., Tan, CH. (2015). Chiral Bicyclic Guanidine, Bis-Guanidinium, Pentanidium and Related Organocatalysts. In: Selig, P. (eds) Guanidines as Reagents and Catalysts I. Topics in Heterocyclic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/7081_2015_175

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