Skip to main content
Log in

Chiral Sulfoxide Ligands in Asymmetric Catalysis

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Noyori R (2003) Adv Synth Catal 345:15

    Article  CAS  Google Scholar 

  2. Knowles WS (2002) Angew Chem Int Ed 41:1998–2007

    Article  CAS  Google Scholar 

  3. Fache F, Schulz E, Tommasino ML, Lemaire M (2000) Chem Rev 100:2159–2232

    Article  CAS  Google Scholar 

  4. Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New York

    Google Scholar 

  5. Jacobsen EN, Pfaltz A, Yamamoto H (1999) Comprehensive asymmetric catalysis. Springer, Berlin

    Book  Google Scholar 

  6. Ojima I (2010) Catalytic asymmetric synthesis, 3rd edn. Wiley, Hoboken

    Book  Google Scholar 

  7. James BR, McMillan RS, Reimer KJ (1976) J Mol Catal 1:439–441

    Article  CAS  Google Scholar 

  8. Fernandez I, Khiar N (2003) Chem Rev 103:3651–3705

    Article  CAS  Google Scholar 

  9. Pellissier H (2007) Tetrahedron 63:1297–1330

    Article  CAS  Google Scholar 

  10. Mellah M, Voituriez A, Schulz E (2007) Chem Rev 107:5133–5209

    Article  CAS  Google Scholar 

  11. Hiroi K, Sone T (2008) Curr Org Synth 5:305–320

    Article  CAS  Google Scholar 

  12. Fernandez I, Khiar N (2008) In: Toru T, Bolm C (eds) Organosulfur chemistry in asymmetric synthesis. Wiley, Weinheim

  13. Trost BM, Rao M (2015) Angew Chem Int Ed 54:5026–5043

    Article  CAS  Google Scholar 

  14. Sipos G, Drinkel EE, Dorta R (2015) Chem Soc Rev 44:3834–3860

    Article  CAS  Google Scholar 

  15. Yamaguchi K, Kondo H, Yamaguchi J, Itami K (2013) Chem Sci 4:3753–3757

    Article  CAS  Google Scholar 

  16. Kondo H, Yu F, Yamaguchi J, Liu GS, Itami K (2014) Org Lett 16:4212–4215

    Article  CAS  Google Scholar 

  17. Ammann SE, Liu W, White MC (2016) Angew Chem Int Ed 55:9571–9575

    Article  CAS  Google Scholar 

  18. Allen JV, Bower JF, Williams JMJ (1994) Tetrahedron Asymmetry 5:1895–1898

    Article  CAS  Google Scholar 

  19. Hiroi K, Watanabe K, Abe I, Koseki M (2001) Tetrahedron Lett 42:7617–7619

    Article  CAS  Google Scholar 

  20. Watanabe K, Hirasawa T, Hiroi K (2002) Chem Pharm Bull 50:372–379

    Article  CAS  Google Scholar 

  21. Chen S, Wu M, Han ZY (2017) Angew Chem Int Ed 56:6641–6645

    Article  CAS  Google Scholar 

  22. Chelucci G, Berta D, Saba A (1997) Tetrahedron 53:3843–3848

    Article  CAS  Google Scholar 

  23. Hiroi K, Suzuki Y (1997) Heterocycles 46:77–81

    Article  CAS  Google Scholar 

  24. Hiroi K, Suzuki Y, Abe I, Hasegawa Y, Suzuki K (1998) Tetrahedron Asymmetry 9:3797–3818

    Article  CAS  Google Scholar 

  25. Petra DGI, Kamer PCJ, Spek AL, Schoemaker HE, van Leeuwen PWNM (2000) J Org Chem 65:3010–3017

    Article  CAS  Google Scholar 

  26. Priego J, Garcia Mancheno O, Cabrera S, Carretero JC (2001) Chem Commun 2026–2027

  27. Priego J, Garcia Mancheno O, Cabrera S, Carretero JC (2002) J Org Chem 67:1346–1353

    Article  CAS  Google Scholar 

  28. Grach G, Reboul V, Metzner P (2008) Tetrahedron Asymmetry 19:1744–1750

    Article  CAS  Google Scholar 

  29. Ekegren JK, Roth P, Kallstrom K, Tarnai T, Andersson PG (2003) Org Biomol Chem 1:358–366

    Article  CAS  Google Scholar 

  30. Tang L, Wang Q, Wang J, Lin Z, Wang X, Cun L, Yuan W, Zhu J, Liao J, Deng J (2012) Tetrahedron Lett 53:3839–3842

    Article  CAS  Google Scholar 

  31. Siedlecka R, Wojaczynska E, Skarzewski J (2004) Tetrahedron Asymmetry 15:1437–1444

    Article  CAS  Google Scholar 

  32. Cheng H-G, Lu L-Q, Wang T, Chen J-R, Xiao W-J (2012) Chem Commun 48:5596–5598

    Article  CAS  Google Scholar 

  33. Hiroi K, Suzuki Y (1998) Tetrahedron Lett 39:6499–6502

    Article  CAS  Google Scholar 

  34. Hiroi K, Suzuki Y, Kawagishi R (1999) Tetrahedron Lett 40:715–718

    Article  CAS  Google Scholar 

  35. Hiroi K, Suzuki Y, Abe I, Kawagishi R (2000) Tetrahedron 56:4701–4710

    Article  CAS  Google Scholar 

  36. Hiroi K, Suzuki Y, Abe I (1999) Chem Lett 149–150

  37. Suzuki Y, Abe I, Hiroi K (1999) Heterocycles 50:89–94

    Article  CAS  Google Scholar 

  38. Hiroi K, Suzuki Y, Abe I (1999) Tetrahedron Asymmetry 10:1173–1188

    Article  CAS  Google Scholar 

  39. Hiroi K, Izawa I, Takizawa T, Kawai K (2004) Tetrahedron 60:2155–2162

    Article  CAS  Google Scholar 

  40. Nakamura S, Fukuzumi T, Toru T (2004) Chirality 16:10–12

    Article  CAS  Google Scholar 

  41. Chen J, Li D, Ma H, Cun L, Zhu J, Deng J, Liao J (2008) Tetrahedron Lett 49:6921–6923

    Article  CAS  Google Scholar 

  42. Yang T, Zhang Y, Cao P, Wang M, Li L, Li D, Liao J (2016) Tetrahedron 72:2707–2711

    Article  CAS  Google Scholar 

  43. Chen J, Lang F, Li D, Cun L, Zhu L, Deng J, Liao J (2009) Tetrahedron Asymmetry 20:1953–1956

    Article  CAS  Google Scholar 

  44. Lang F, Li D, Chen J, Chen J, Li L, Cun L, Zhu J, Deng J, Liao J (2010) Adv Synth Catal 352:843–846

    Article  CAS  Google Scholar 

  45. Chen G, Xing J, Cao P, Liao J (2012) Tetrahedron 68:5908–5911

    Article  CAS  Google Scholar 

  46. Gui J, Chen G, Cao P, Liao J (2012) Tetrahedron Asymmetry 23:554–563

    Article  CAS  Google Scholar 

  47. Lang F, Chen G, Li L, Xing J, Han F, Cun L, Liao J (2011) Chem Eur J 17:5242–5245

    Article  CAS  Google Scholar 

  48. Xing J, Chen G, Cao P, Liao J (2012) Eur J Org Chem 1230–1236

  49. Du L, Cao P, Xing J, Lou Y, Jiang L, Li L, Liao J (2013) Angew Chem Int Ed 52:4207–4211

    Article  CAS  Google Scholar 

  50. Wang JJ, Wang M, Cao P, Jiang LY, Chen GH, Liao J (2014) Angew Chem Int Ed 53:6673–6677

    Article  CAS  Google Scholar 

  51. Li L, Sun R, Zheng R, Huang Y, Chen H (2018) Eur J Org Chem 3426–3431

  52. Wang JJ, Wang B, Cao P, Liao J (2014) Tetrahedron Lett 55:3450–3453

    Article  CAS  Google Scholar 

  53. Jia T, Cao P, Wang D, Lou Y, Liao J (2015) Chem Eur J 21:4918–4922

    Article  CAS  Google Scholar 

  54. Wang D, Cao P, Wang B, Jia T, Lou Y, Wang M, Liao J (2015) Org Lett 17:2420–2423

    Article  CAS  Google Scholar 

  55. Lou Y, Cao P, Jia T, Zhang Y, Wang M, Liao J (2015) Angew Chem Int Ed 54:12134–12138

    Article  CAS  Google Scholar 

  56. Jia T, Cao P, Wang B, Lou Y, Yin X, Wang M, Liao J (2015) J Am Chem Soc 137:13760–13763

    Article  CAS  Google Scholar 

  57. Chen B, Cao P, Yin X, Liao Y, Jiang L, Ye J, Wang M, Liao J (2017) ACS Catal 7:2425–2429

    Article  CAS  Google Scholar 

  58. Chen B, Cao P, Liao Y, Wang M, Liao J (2018) Org Lett 20:1346–1349

    Article  CAS  Google Scholar 

  59. Cheng HG, Feng B, Chen LY, Guo W, Yu XY, Lu LQ, Chen JR, Xiao WJ (2014) Chem Commun 50:2873

    Article  CAS  Google Scholar 

  60. Feng B, Cheng HG, Chen JR, Deng QH, Lu LQ, Xiao WJ (2014) Chem Commun 50:9550–9955

    Article  CAS  Google Scholar 

  61. Tokunoh R, Sodeoka M, Aoe K, Shibasaki M (1995) Tetrahedron Lett 36:8035–8038

    Article  CAS  Google Scholar 

  62. Mariz R, Luan X, Gatti M, Linden A, Dorta R (2008) J Am Chem Soc 130:2172–2173

    Article  CAS  Google Scholar 

  63. Burgi JJ, Mariz R, Gatti M, Drinkel E, Luan X, Blumentritt S, Linden A, Dorta R (2009) Angew Chem Int Ed 48:2768–2771

    Article  Google Scholar 

  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 16:14335–14347

    Article  CAS  Google Scholar 

  65. Poater A, Ragone F, Mariz R, Dorta R, Cavallo L (2010) Chem Eur J 16:14348–14353

    Article  CAS  Google Scholar 

  66. Chen QA, Dong X, Chen MW, Wang DS, Zhou YG, Li YX (2010) Org Lett 12:1928–1931

    Article  CAS  Google Scholar 

  67. Chen J, Chen J, Lang F, Zhang X, Cun L, Zhu J, Deng J, Liao J (2010) J Am Chem Soc 132:4552–4553

    Article  CAS  Google Scholar 

  68. Zhang X, Chen J, Han F, Cun L, Liao J (2011) Eur J Org Chem :1443–1446

  69. Han F, Chen J, Zhang X, Liu J, Cun L, Zhu J, Deng J, Liao J (2011) Tetrahedron Lett 52:830–833

    Article  CAS  Google Scholar 

  70. Han F, Chen G, Zhang X, Liao J (2011) Eur J Org Chem :2928–2931

  71. Dornan PK, Leung PL, Dong VM (2011) Tetrahedron 67:4378–4384

    Article  CAS  Google Scholar 

  72. Khiar N, Salvador A, Valdivia V, Chelouan A, Alucdia A, Lvarez F, Fernndez I (2013) J Org Chem 78:6510–6521

    Article  CAS  Google Scholar 

  73. Liu J, Chen G, Xing J, Liao J (2011) Tetrahedron Asymmetry 22:575–579

    Article  CAS  Google Scholar 

  74. Shintani R, Hayashi T (2009) Aldrichim Acta 42:31

    CAS  Google Scholar 

  75. Defieber C, Grutzmacher H, Carreira EM (2008) Angew Chem Int Ed 47:4482

    Article  CAS  Google Scholar 

  76. Thaler T, Guo LN, Steib AK, Raducan M, Karaghiosoff K, Mayer P, Knochel P (2011) Org Lett 13:3182–3185

    Article  CAS  Google Scholar 

  77. Chen G, Gui J, Li L, Liao J (2011) Angew Chem Int Ed 50:7681–7685

    Article  CAS  Google Scholar 

  78. Chen G, Gui J, Li L, Liao J (2011) Angew Chem 2011(123):7823–7827

    Article  Google Scholar 

  79. Chen G, Gui J, Cao P, Liao J (2012) Tetrahedron 68:3220–3224

    Article  CAS  Google Scholar 

  80. Qi W-Y, Zhu T-S, Xu M-H (2011) Org Lett 13:3410–3413

    Article  CAS  Google Scholar 

  81. Xue F, Li X, Wan B (2011) J Org Chem 76:7256–7262

    Article  CAS  Google Scholar 

  82. Xue F, Wang D, Li X, Wan B (2012) J Org Chem 77:3071–3081

    Article  CAS  Google Scholar 

  83. Xue F, Wang D, Li X, Wan B (2013) Org Biomol Chem 11:7893–7898

    Article  CAS  Google Scholar 

  84. Trost BM, Rao M, Dieskau AP (2013) J Am Chem Soc 135:18697–18704

    Article  CAS  Google Scholar 

  85. Trost BM, Ryan MC, Rao M, Markovic TZ (2014) J Am Chem Soc 136:17422–17425

    Article  CAS  Google Scholar 

  86. Rowlands GJ (2003) Synlett :236–240

  87. Ichikawa E, Suzuki M, Yabu K, Albert M, Kanai M, Shibasaki M (2004) J Am Chem Soc 126:11808–11809

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jian Liao.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jia, T., Wang, M. & Liao, J. Chiral Sulfoxide Ligands in Asymmetric Catalysis. Top Curr Chem (Z) 377, 8 (2019). https://doi.org/10.1007/s41061-019-0232-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-019-0232-9

Keywords

Navigation