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Asymmetric Synthesis Using Thioamides

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Chemistry of Thioamides

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Abstract

Following the preceding chapter in which synthesis and transformation of thioamides were introduced, this chapter provides an overview of state-of-the-art asymmetric catalysis to elicit the hidden reactivity of thioamide functionality, thereby engaging thioamide substrates in catalytic transformations to produce more elaborate thioamide compounds. The designed catalytic systems, comprising a soft Lewis acid and Brønsted base, chemoselectively activate thioamides in both a nucleophilic and electrophilic fashion, leading to a number of bimolecular reactions rendered catalytic and enantioselective. The last section showcases the synthetic application of these catalytic processes to demonstrate their practical utility.

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References

  1. T.S. Jagodziński, Chem. Rev. 103, 197–227 (2003)

    Article  Google Scholar 

  2. Z. Liu, H. Qu, X. Gu, B.J. Min, J. Nyberg, V.J. Hruby, Org. Lett. 10, 4105–4108 (2008)

    Article  CAS  Google Scholar 

  3. J.T. Reeves, Z. Tan, M.A. Herbage, Z.S. Han, M.A. Marsini, Z. Li, G. Li, Y. Xu, K.R. Fandrick, N.C. Gonnella, S. Campbell, S. Ma, N. Grinberg, H. Lee, B.Z. Lu, C.H. Senanayake, J. Am. Chem. Soc. 135, 5565–5568 (2013)

    Article  CAS  Google Scholar 

  4. H. Yamamoto, K. Futatsugi, Angew. Chem. Int. Ed. 44, 1924–1942 (2005)

    Article  CAS  Google Scholar 

  5. H. Yamamoto, K. Ishihara, Acid Catalysis in Modern Organic Synthesis (Wiley-VCH; Wiley, Weinheim, 2008)

    Google Scholar 

  6. Y. Tamaru, T. Harada, S.-I. Nishi, M. Mizutani, T. Hioki, Z.-I. Yoshida, J. Am. Chem. Soc. 102, 7806–7808 (1980)

    Article  CAS  Google Scholar 

  7. Y. Tamaru, T. Hioki, Z. Yoshida, Tetrahedron Lett. 25, 5793–5796 (1984)

    Article  CAS  Google Scholar 

  8. C. Goasdoue, N. Goasdoue, M. Gaudemar, J. Organomet. Chem. 208, 279–292 (1981)

    Article  CAS  Google Scholar 

  9. C. Goasdoue, N. Goasdoue, M. Gaudemar, Tetrahedron Lett. 24, 4001–4004 (1983)

    Article  CAS  Google Scholar 

  10. C. Goasdoue, N. Goasdoue, M. Gaudemar, J. Organomet. Chem. 263, 273–281 (1984)

    Article  CAS  Google Scholar 

  11. N. Iwasawa, T. Yura, T. Mukaiyama, Tetrahedron 45, 1197–1207 (1989)

    Article  CAS  Google Scholar 

  12. N. Kumagai, Chem. Pharm. Bull. 59, 1–22 (2011)

    Article  CAS  Google Scholar 

  13. N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 50, 4760–4772 (2011)

    Article  CAS  Google Scholar 

  14. N. Kumagai, M. Shibasaki, Isr. J. Chem. 52, 604–612 (2012)

    Article  CAS  Google Scholar 

  15. B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595–1601 (2002)

    Article  Google Scholar 

  16. R. Mahrwald, Modern Aldol Reactions (Wiley-VCH, Weinheim, 2004)

    Book  Google Scholar 

  17. W. Notz, F. Tanaka, C.F. Barbas III, Acc. Chem. Res. 37, 580–591 (2004)

    Article  CAS  Google Scholar 

  18. S. Mukherjee, J.W. Yang, S. Hoffmann, B. List, Chem. Rev. 107, 5471–5569 (2007)

    Article  CAS  Google Scholar 

  19. B.M. Trost, C.S. Brindle, Chem. Soc. Rev. 39, 1600–1632 (2010)

    Article  CAS  Google Scholar 

  20. R. Mahrwald, Modern Methods in Stereoselective Aldol Reactions (Wiley-VCH, Weinheim, 2013)

    Book  Google Scholar 

  21. Y.M.A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. Int. Ed. Engl. 36, 1871–1873 (1997)

    Article  CAS  Google Scholar 

  22. N. Yoshikawa, Y.M.A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 121, 4168–4178 (1999)

    Article  CAS  Google Scholar 

  23. B. List, R.A. Lerner, C.F. Barbas III, J. Am. Chem. Soc. 122, 2395–2396 (2000)

    Article  CAS  Google Scholar 

  24. B.M. Trost, H. Ito, J. Am. Chem. Soc. 122, 12003–12004 (2000)

    Article  CAS  Google Scholar 

  25. M. Shibasaki, N. Yoshikawa, Chem. Rev. 102, 2187–2209 (2002)

    Article  CAS  Google Scholar 

  26. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491–1508 (2005)

    Article  Google Scholar 

  27. D.H. Paull, C.J. Abraham, M.T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 41, 655–663 (2008)

    Article  CAS  Google Scholar 

  28. R. Peters, Cooperative Catalysis (Wiley-VCH, Weinheim, 2015)

    Book  Google Scholar 

  29. M. Iwata, R. Yazaki, Y. Suzuki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 131, 18244–18245 (2009)

    Article  CAS  Google Scholar 

  30. M. Iwata, R. Yazaki, I.H. Chen, D. Sureshkumar, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 133, 5554–5560 (2011)

    Article  CAS  Google Scholar 

  31. Y. Bao, N. Kumagai, M. Shibasaki, Chem. Sci. 6, 6124–6132 (2015)

    Article  CAS  Google Scholar 

  32. T. Tsuda, T. Yazawa, K. Watanabe, T. Fujii, T. Saegusa, J. Org. Chem. 46, 192–194 (1981)

    Article  CAS  Google Scholar 

  33. E.M. Meyer, S. Gambarotta, C. Floriani, A. Chiesi-Villa, C. Guastinit, Organometallics 8, 1067–1079 (1989)

    Article  CAS  Google Scholar 

  34. M. Stollenz, F. Meyer, Organometallics 31, 7708–7727 (2012)

    Article  CAS  Google Scholar 

  35. J. Cui, A. Ohtsuki, T. Watanabe, N. Kumagai, M. Shibasaki, Chem. Eur. J. 24, 2598–2601 (2018)

    Article  CAS  Google Scholar 

  36. D. Sureshkumar, Y. Kawato, M. Iwata, N. Kumagai, M. Shibasaki, Org. Lett. 14, 3108–3111 (2012)

    Article  CAS  Google Scholar 

  37. Y. Suzuki, R. Yazaki, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 48, 5026–5029 (2009)

    Article  CAS  Google Scholar 

  38. Y. Suzuki, R. Yazaki, N. Kumagai, M. Shibasaki, Chem. Eur. J. 17, 11998–12001 (2011)

    Article  CAS  Google Scholar 

  39. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 132, 10275–10277 (2010)

    Article  CAS  Google Scholar 

  40. R. Yazaki, N. Kumagai, M. Shibasaki, Chem. Asian J. 6, 1778–1790 (2011)

    Article  CAS  Google Scholar 

  41. Y. Yanagida, R. Yazaki, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 50, 7910–7914 (2011)

    Article  CAS  Google Scholar 

  42. N. Majumdar, A. Saito, L. Yin, N. Kumagai, M. Shibasaki, Org. Lett. 17, 3362–3365 (2015)

    Article  CAS  Google Scholar 

  43. T. Ogawa, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 51, 8551–8554 (2012)

    Article  CAS  Google Scholar 

  44. T. Ogawa, S. Mouri, R. Yazakinaoya, N. Kumagai, M. Shibasaki, Org. Lett. 14, 110–113 (2012)

    Article  CAS  Google Scholar 

  45. L. Yin, H. Takada, S. Lin, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 53, 5327–5331 (2014)

    Article  CAS  Google Scholar 

  46. D.A. Evans, E. Vogel, J.V. Nelson, J. Am. Chem. Soc. 101, 6120–6123 (1979)

    Article  CAS  Google Scholar 

  47. D.A. Evans, J. Bartroli, T.L. Shih, J. Am. Chem. Soc. 103, 2127–2129 (1981)

    Article  CAS  Google Scholar 

  48. D.A. Evans, Aldrichmica Acta 15, 23–32 (1982)

    CAS  Google Scholar 

  49. P. Gopinath, T. Watanabe, M. Shibasaki, J. Org. Chem. 77, 9260–9267 (2012)

    Article  CAS  Google Scholar 

  50. H. Abe, P. Gopinath, G. Ravi, L. Wang, T. Watanabe, M. Shibasaki, Tetrahedron Lett. 56, 3782–3785 (2015)

    Article  CAS  Google Scholar 

  51. H. Abe, H. Ouchi, C. Sakashita, M. Kawada, T. Watanabe, M. Shibasaki, Chem. Eur. J. 23, 11792–11796 (2017)

    Article  CAS  Google Scholar 

  52. H. Abe, M. Kawada, C. Sakashita, T. Watanabe, M. Shibasaki, Tetrahedron 74, 5129–5137 (2018)

    Article  CAS  Google Scholar 

  53. Y. Sahara, J. Cui, M. Furutachi, J. Chen, T. Watanabe, M. Shibasaki, Synthesis 49, 69–75 (2016)

    Article  Google Scholar 

  54. Y. Kawato, M. Iwata, R. Yazaki, N. Kumagai, M. Shibasaki, Tetrahedron 67, 6539–6546 (2011)

    Article  CAS  Google Scholar 

  55. Y. Kawato, S. Chaudhary, N. Kumagai, M. Shibasaki, Chem. Eur. J. 19, 3802–3806 (2013)

    Article  CAS  Google Scholar 

  56. Iwata M, Yazaki R, Kumagai N, Shibasaki M, Tetrahedron: asymmetry 21:1688–1694 (2010)

    Article  CAS  Google Scholar 

  57. Y. Suzuki, M. Iwata, R. Yazaki, N. Kumagai, M. Shibasaki, J. Org. Chem. 77, 4496–4500 (2012)

    Article  CAS  Google Scholar 

  58. J. Cui, M. Morita, O. Ohno, T. Kimura, T. Teruya, T. Watanabe, K. Suenaga, M. Shibasaki, Chem. Eur. J. 23, 8500–8509 (2017)

    Article  CAS  Google Scholar 

  59. J. Cui, T. Watanabe, M. Shibasaki, Tetrahedron Lett. 57, 446–448 (2016)

    Article  CAS  Google Scholar 

  60. A. Matsuzawa, C.R. Opie, N. Kumagai, M. Shibasaki, Chem. Eur. J. 20, 68–71 (2014)

    Article  CAS  Google Scholar 

  61. K. Alagiri, S. Lin, N. Kumagai, M. Shibasaki, Org. Lett. 16, 5301–5303 (2014)

    Article  CAS  Google Scholar 

  62. R. Yazaki, N. Kumagai, M. Shibasaki, Org. Lett. 13, 952–955 (2011)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-Ku, Tokyo, 141-0021, Japan

    Naoya Kumagai & Masakatsu Shibasaki

Authors
  1. Naoya Kumagai
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  2. Masakatsu Shibasaki
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Correspondence to Naoya Kumagai or Masakatsu Shibasaki .

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Editors and Affiliations

  1. Gifu University, Gifu, Japan

    Toshiaki Murai

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Kumagai, N., Shibasaki, M. (2019). Asymmetric Synthesis Using Thioamides. In: Murai, T. (eds) Chemistry of Thioamides. Springer, Singapore. https://doi.org/10.1007/978-981-13-7828-7_5

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