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Chiral Sulfoxide Ligands in Asymmetric Catalysis

  • Tao Jia
  • Min Wang
  • Jian LiaoEmail author
Review
Part of the following topical collections:
  1. Sulfur Chemistry

Abstract

Since the original idea was explored by James in 1976, the use of chiral sulfoxides as ligands with transition metals in asymmetric catalysis has undergone a long period of development. There have been many studies into their properties, design and application in various kinds of asymmetric transformations. In this article, we document the literatures on chiral sulfoxide ligands in asymmetric catalytic reactions.

Keywords

Chiral sulfoxide ligands S-chirality Transition-metal Asymmetric catalysis 

Notes

Acknowledgements

We thank the National Nature Science Foundation of China (No. 21871251 and 21472184), the Biological Resources Network of Chinese Academy of Sciences (No. ZSTH-030) and Sichuan Sci&Tech Department (2016 JZ0022) for financial support.

References

  1. 1.
    Noyori R (2003) Adv Synth Catal 345:15CrossRefGoogle Scholar
  2. 2.
    Knowles WS (2002) Angew Chem Int Ed 41:1998–2007CrossRefGoogle Scholar
  3. 3.
    Fache F, Schulz E, Tommasino ML, Lemaire M (2000) Chem Rev 100:2159–2232PubMedCrossRefGoogle Scholar
  4. 4.
    Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New YorkGoogle Scholar
  5. 5.
    Jacobsen EN, Pfaltz A, Yamamoto H (1999) Comprehensive asymmetric catalysis. Springer, BerlinCrossRefGoogle Scholar
  6. 6.
    Ojima I (2010) Catalytic asymmetric synthesis, 3rd edn. Wiley, HobokenCrossRefGoogle Scholar
  7. 7.
    James BR, McMillan RS, Reimer KJ (1976) J Mol Catal 1:439–441CrossRefGoogle Scholar
  8. 8.
    Fernandez I, Khiar N (2003) Chem Rev 103:3651–3705PubMedCrossRefGoogle Scholar
  9. 9.
    Pellissier H (2007) Tetrahedron 63:1297–1330CrossRefGoogle Scholar
  10. 10.
    Mellah M, Voituriez A, Schulz E (2007) Chem Rev 107:5133–5209PubMedCrossRefGoogle Scholar
  11. 11.
    Hiroi K, Sone T (2008) Curr Org Synth 5:305–320CrossRefGoogle Scholar
  12. 12.
    Fernandez I, Khiar N (2008) In: Toru T, Bolm C (eds) Organosulfur chemistry in asymmetric synthesis. Wiley, WeinheimGoogle Scholar
  13. 13.
    Trost BM, Rao M (2015) Angew Chem Int Ed 54:5026–5043CrossRefGoogle Scholar
  14. 14.
    Sipos G, Drinkel EE, Dorta R (2015) Chem Soc Rev 44:3834–3860PubMedCrossRefGoogle Scholar
  15. 15.
    Yamaguchi K, Kondo H, Yamaguchi J, Itami K (2013) Chem Sci 4:3753–3757CrossRefGoogle Scholar
  16. 16.
    Kondo H, Yu F, Yamaguchi J, Liu GS, Itami K (2014) Org Lett 16:4212–4215PubMedCrossRefGoogle Scholar
  17. 17.
    Ammann SE, Liu W, White MC (2016) Angew Chem Int Ed 55:9571–9575CrossRefGoogle Scholar
  18. 18.
    Allen JV, Bower JF, Williams JMJ (1994) Tetrahedron Asymmetry 5:1895–1898CrossRefGoogle Scholar
  19. 19.
    Hiroi K, Watanabe K, Abe I, Koseki M (2001) Tetrahedron Lett 42:7617–7619CrossRefGoogle Scholar
  20. 20.
    Watanabe K, Hirasawa T, Hiroi K (2002) Chem Pharm Bull 50:372–379PubMedCrossRefGoogle Scholar
  21. 21.
    Chen S, Wu M, Han ZY (2017) Angew Chem Int Ed 56:6641–6645CrossRefGoogle Scholar
  22. 22.
    Chelucci G, Berta D, Saba A (1997) Tetrahedron 53:3843–3848CrossRefGoogle Scholar
  23. 23.
    Hiroi K, Suzuki Y (1997) Heterocycles 46:77–81CrossRefGoogle Scholar
  24. 24.
    Hiroi K, Suzuki Y, Abe I, Hasegawa Y, Suzuki K (1998) Tetrahedron Asymmetry 9:3797–3818CrossRefGoogle Scholar
  25. 25.
    Petra DGI, Kamer PCJ, Spek AL, Schoemaker HE, van Leeuwen PWNM (2000) J Org Chem 65:3010–3017PubMedCrossRefGoogle Scholar
  26. 26.
    Priego J, Garcia Mancheno O, Cabrera S, Carretero JC (2001) Chem Commun 2026–2027Google Scholar
  27. 27.
    Priego J, Garcia Mancheno O, Cabrera S, Carretero JC (2002) J Org Chem 67:1346–1353PubMedCrossRefGoogle Scholar
  28. 28.
    Grach G, Reboul V, Metzner P (2008) Tetrahedron Asymmetry 19:1744–1750CrossRefGoogle Scholar
  29. 29.
    Ekegren JK, Roth P, Kallstrom K, Tarnai T, Andersson PG (2003) Org Biomol Chem 1:358–366PubMedCrossRefGoogle Scholar
  30. 30.
    Tang L, Wang Q, Wang J, Lin Z, Wang X, Cun L, Yuan W, Zhu J, Liao J, Deng J (2012) Tetrahedron Lett 53:3839–3842CrossRefGoogle Scholar
  31. 31.
    Siedlecka R, Wojaczynska E, Skarzewski J (2004) Tetrahedron Asymmetry 15:1437–1444CrossRefGoogle Scholar
  32. 32.
    Cheng H-G, Lu L-Q, Wang T, Chen J-R, Xiao W-J (2012) Chem Commun 48:5596–5598CrossRefGoogle Scholar
  33. 33.
    Hiroi K, Suzuki Y (1998) Tetrahedron Lett 39:6499–6502CrossRefGoogle Scholar
  34. 34.
    Hiroi K, Suzuki Y, Kawagishi R (1999) Tetrahedron Lett 40:715–718CrossRefGoogle Scholar
  35. 35.
    Hiroi K, Suzuki Y, Abe I, Kawagishi R (2000) Tetrahedron 56:4701–4710CrossRefGoogle Scholar
  36. 36.
    Hiroi K, Suzuki Y, Abe I (1999) Chem Lett 149–150Google Scholar
  37. 37.
    Suzuki Y, Abe I, Hiroi K (1999) Heterocycles 50:89–94CrossRefGoogle Scholar
  38. 38.
    Hiroi K, Suzuki Y, Abe I (1999) Tetrahedron Asymmetry 10:1173–1188CrossRefGoogle Scholar
  39. 39.
    Hiroi K, Izawa I, Takizawa T, Kawai K (2004) Tetrahedron 60:2155–2162CrossRefGoogle Scholar
  40. 40.
    Nakamura S, Fukuzumi T, Toru T (2004) Chirality 16:10–12PubMedCrossRefGoogle Scholar
  41. 41.
    Chen J, Li D, Ma H, Cun L, Zhu J, Deng J, Liao J (2008) Tetrahedron Lett 49:6921–6923CrossRefGoogle Scholar
  42. 42.
    Yang T, Zhang Y, Cao P, Wang M, Li L, Li D, Liao J (2016) Tetrahedron 72:2707–2711CrossRefGoogle Scholar
  43. 43.
    Chen J, Lang F, Li D, Cun L, Zhu L, Deng J, Liao J (2009) Tetrahedron Asymmetry 20:1953–1956CrossRefGoogle Scholar
  44. 44.
    Lang F, Li D, Chen J, Chen J, Li L, Cun L, Zhu J, Deng J, Liao J (2010) Adv Synth Catal 352:843–846CrossRefGoogle Scholar
  45. 45.
    Chen G, Xing J, Cao P, Liao J (2012) Tetrahedron 68:5908–5911CrossRefGoogle Scholar
  46. 46.
    Gui J, Chen G, Cao P, Liao J (2012) Tetrahedron Asymmetry 23:554–563CrossRefGoogle Scholar
  47. 47.
    Lang F, Chen G, Li L, Xing J, Han F, Cun L, Liao J (2011) Chem Eur J 17:5242–5245PubMedCrossRefGoogle Scholar
  48. 48.
    Xing J, Chen G, Cao P, Liao J (2012) Eur J Org Chem 1230–1236Google Scholar
  49. 49.
    Du L, Cao P, Xing J, Lou Y, Jiang L, Li L, Liao J (2013) Angew Chem Int Ed 52:4207–4211CrossRefGoogle Scholar
  50. 50.
    Wang JJ, Wang M, Cao P, Jiang LY, Chen GH, Liao J (2014) Angew Chem Int Ed 53:6673–6677CrossRefGoogle Scholar
  51. 51.
    Li L, Sun R, Zheng R, Huang Y, Chen H (2018) Eur J Org Chem 3426–3431Google Scholar
  52. 52.
    Wang JJ, Wang B, Cao P, Liao J (2014) Tetrahedron Lett 55:3450–3453CrossRefGoogle Scholar
  53. 53.
    Jia T, Cao P, Wang D, Lou Y, Liao J (2015) Chem Eur J 21:4918–4922PubMedCrossRefGoogle Scholar
  54. 54.
    Wang D, Cao P, Wang B, Jia T, Lou Y, Wang M, Liao J (2015) Org Lett 17:2420–2423PubMedCrossRefGoogle Scholar
  55. 55.
    Lou Y, Cao P, Jia T, Zhang Y, Wang M, Liao J (2015) Angew Chem Int Ed 54:12134–12138CrossRefGoogle Scholar
  56. 56.
    Jia T, Cao P, Wang B, Lou Y, Yin X, Wang M, Liao J (2015) J Am Chem Soc 137:13760–13763PubMedCrossRefGoogle Scholar
  57. 57.
    Chen B, Cao P, Yin X, Liao Y, Jiang L, Ye J, Wang M, Liao J (2017) ACS Catal 7:2425–2429CrossRefGoogle Scholar
  58. 58.
    Chen B, Cao P, Liao Y, Wang M, Liao J (2018) Org Lett 20:1346–1349PubMedCrossRefGoogle Scholar
  59. 59.
    Cheng HG, Feng B, Chen LY, Guo W, Yu XY, Lu LQ, Chen JR, Xiao WJ (2014) Chem Commun 50:2873CrossRefGoogle Scholar
  60. 60.
    Feng B, Cheng HG, Chen JR, Deng QH, Lu LQ, Xiao WJ (2014) Chem Commun 50:9550–9955CrossRefGoogle Scholar
  61. 61.
    Tokunoh R, Sodeoka M, Aoe K, Shibasaki M (1995) Tetrahedron Lett 36:8035–8038CrossRefGoogle Scholar
  62. 62.
    Mariz R, Luan X, Gatti M, Linden A, Dorta R (2008) J Am Chem Soc 130:2172–2173PubMedCrossRefGoogle Scholar
  63. 63.
    Burgi JJ, Mariz R, Gatti M, Drinkel E, Luan X, Blumentritt S, Linden A, Dorta R (2009) Angew Chem Int Ed 48:2768–2771CrossRefGoogle Scholar
  64. 64.
    Mariz R, Poater A, Gatti M, Drinkel E, Burgi JJ, Luan X, Blumentritt S, Linden A, Cavallo L, Dorta R (2010) Chem Eur J 16:14335–14347PubMedCrossRefGoogle Scholar
  65. 65.
    Poater A, Ragone F, Mariz R, Dorta R, Cavallo L (2010) Chem Eur J 16:14348–14353PubMedCrossRefGoogle Scholar
  66. 66.
    Chen QA, Dong X, Chen MW, Wang DS, Zhou YG, Li YX (2010) Org Lett 12:1928–1931PubMedCrossRefGoogle Scholar
  67. 67.
    Chen J, Chen J, Lang F, Zhang X, Cun L, Zhu J, Deng J, Liao J (2010) J Am Chem Soc 132:4552–4553PubMedCrossRefGoogle Scholar
  68. 68.
    Zhang X, Chen J, Han F, Cun L, Liao J (2011) Eur J Org Chem :1443–1446Google Scholar
  69. 69.
    Han F, Chen J, Zhang X, Liu J, Cun L, Zhu J, Deng J, Liao J (2011) Tetrahedron Lett 52:830–833CrossRefGoogle Scholar
  70. 70.
    Han F, Chen G, Zhang X, Liao J (2011) Eur J Org Chem :2928–2931Google Scholar
  71. 71.
    Dornan PK, Leung PL, Dong VM (2011) Tetrahedron 67:4378–4384CrossRefGoogle Scholar
  72. 72.
    Khiar N, Salvador A, Valdivia V, Chelouan A, Alucdia A, Lvarez F, Fernndez I (2013) J Org Chem 78:6510–6521PubMedCrossRefGoogle Scholar
  73. 73.
    Liu J, Chen G, Xing J, Liao J (2011) Tetrahedron Asymmetry 22:575–579CrossRefGoogle Scholar
  74. 74.
    Shintani R, Hayashi T (2009) Aldrichim Acta 42:31Google Scholar
  75. 75.
    Defieber C, Grutzmacher H, Carreira EM (2008) Angew Chem Int Ed 47:4482CrossRefGoogle Scholar
  76. 76.
    Thaler T, Guo LN, Steib AK, Raducan M, Karaghiosoff K, Mayer P, Knochel P (2011) Org Lett 13:3182–3185PubMedCrossRefGoogle Scholar
  77. 77.
    Chen G, Gui J, Li L, Liao J (2011) Angew Chem Int Ed 50:7681–7685CrossRefGoogle Scholar
  78. 78.
    Chen G, Gui J, Li L, Liao J (2011) Angew Chem 2011(123):7823–7827CrossRefGoogle Scholar
  79. 79.
    Chen G, Gui J, Cao P, Liao J (2012) Tetrahedron 68:3220–3224CrossRefGoogle Scholar
  80. 80.
    Qi W-Y, Zhu T-S, Xu M-H (2011) Org Lett 13:3410–3413PubMedCrossRefGoogle Scholar
  81. 81.
    Xue F, Li X, Wan B (2011) J Org Chem 76:7256–7262PubMedCrossRefGoogle Scholar
  82. 82.
    Xue F, Wang D, Li X, Wan B (2012) J Org Chem 77:3071–3081PubMedCrossRefGoogle Scholar
  83. 83.
    Xue F, Wang D, Li X, Wan B (2013) Org Biomol Chem 11:7893–7898PubMedCrossRefGoogle Scholar
  84. 84.
    Trost BM, Rao M, Dieskau AP (2013) J Am Chem Soc 135:18697–18704PubMedCrossRefGoogle Scholar
  85. 85.
    Trost BM, Ryan MC, Rao M, Markovic TZ (2014) J Am Chem Soc 136:17422–17425PubMedCrossRefGoogle Scholar
  86. 86.
    Rowlands GJ (2003) Synlett :236–240Google Scholar
  87. 87.
    Ichikawa E, Suzuki M, Yabu K, Albert M, Kanai M, Shibasaki M (2004) J Am Chem Soc 126:11808–11809PubMedCrossRefGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Chengdu Institute of BiologyChinese Academy of SciencesChengduChina
  2. 2.College of Chemical EngineeringSichuan UniversityChengduChina

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