Skip to main content

Advertisement

Log in

Modern Approaches to Synthetic Design of Chiral α-Tertiary Amines Based on Trifluoromethylcontaining Ketimines: A Review

  • Published:
Theoretical and Experimental Chemistry Aims and scope

Enantioselective construction methods of chiral derivatives of α-tertiary amines using acyclic and cyclic trifluoromethylketimines are considered. The importance of a trifluoromethyl group in the structure of ketimine substrates for effective asymmetric addition of C-nucleophilic reagents in the presence of metal complex catalysts or organocatalysts is emphasized. The practical application of these chiral products in medicinal chemistry is covered.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 40

Similar content being viewed by others

References

  1. K. Eller, E. Henkes, R. Rossbacher, et al., Amines, Aliphatic to Antibiotics. Ullmann’s Encyclopedia of Industrial Chemistry, John Wiley & Sons (2000).

  2. D. Vasu, A. L. de Arriba, J. A. Leitch, et al., Chem. Sci., 10, No. 11, 3401-3407 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. T. C. Nugent and M. El-Shazly, Adv. Synth. Cat., 352, No. 5, 753-819 (2010).

    Article  CAS  Google Scholar 

  4. S. Kobayashi, Y. Mori, J. S. Fossey, et al., Chem. Rev., 111, No. 4, 2626-2704 (2011).

    Article  CAS  PubMed  Google Scholar 

  5. A. Noble and J. C. Anderson, Chem. Rev., 113, No. 5, 2887-2939 (2013).

    Article  CAS  PubMed  Google Scholar 

  6. B. M. Trost, Science, 254, No. 5037, 1471-1477 (1991).

    Article  CAS  PubMed  Google Scholar 

  7. N. Kumagai and M. Shibasaki, Bull. Chem. Soc. Jpn., 503-517 (2015).

  8. O. Riant and J. Hannedouche, Org. Biomol. Chem., 5, No. 6, 873-888 (2007).

    Article  CAS  PubMed  Google Scholar 

  9. M. Shibasaki and M. Kanai, Chem. Rev., 108, No. 8, 2853-2873 (2008).

    Article  CAS  PubMed  Google Scholar 

  10. J. Wang, M. Sanchez-Rosello, J. L. Acena, et al., Chem. Rev., 114, No. 4, 2432-2506 (2014).

    Article  CAS  PubMed  Google Scholar 

  11. Y. Zhou, J. Wang, Z. Gu, et al., Chem. Rev., 116, No. 2, 422-518 (2016).

    Article  CAS  PubMed  Google Scholar 

  12. J. Nie, H.-C. Guo, D. Cahard, et al., Chem. Rev., 111, No. 2, 455-529 (2011).

    Article  CAS  PubMed  Google Scholar 

  13. M. Sani, A. Volonterio, and M. Zanda, ChemMedChem., 2, No. 12, 1693-1700 (2007).

    Article  CAS  PubMed  Google Scholar 

  14. M. Morgenthaler, E. Schweizer, A. Hoffmann-Roder, et al., ChemMedChem., 2, No. 8, 1100-1115 (2007).

    Article  CAS  PubMed  Google Scholar 

  15. G. Chaume, M. -C. Van Severen, L. Ricard, et al., J. Fluor. Chem., 129, No. 11, 1104-1109 (2008).

    Article  CAS  Google Scholar 

  16. T. B. Hurley, S. Peukert, and S. Wattanasin, Inhibitors of Undecaprenyl Pyrophosphate Synthase, Patent US 2009203694 (A1), Publ. 2009.

  17. J. Simon, E. Chelain, and T. Brigaud, Org. Lett., 14, No. 2, 604-607 (2012).

    Article  CAS  PubMed  Google Scholar 

  18. E. Aktoudianakis, G. Chin, R. L. Mackman, et al., Toll Like Receptor Modulator Compounds, Patent US 20160289229 (A1), Publ. 2016.

  19. J. J. Bronson, L. Chen, J. L. Ditta, et al., Biaryl Kinase Inhibitors, Patent WO 2017059080 (A1), Publ. 2017.

  20. Q. Gao, Y. Wang, J. Hou, et al., J. Comput. Aided Mol. Des., 31, No. 7, 625-641 (2017).

    Article  CAS  PubMed  Google Scholar 

  21. R. Sinisi, M. Sani, G. Candiani, et al., Tetrahedron Lett., 46, No. 38, 6515-6518 (2005).

    Article  CAS  Google Scholar 

  22. Y. Firsova, N. E. Lozinskaya, S. Sosonyuk, et al., Rev. J. Chem., 2, No. 1, 74-104 (2012).

    Article  Google Scholar 

  23. A. M. Rouh, Chem. Eng. News, 82, No. 24, 47-62 (2004).

    Article  Google Scholar 

  24. A. Berkessel and H. Groger, Organocatalysis – From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis, Wiley-WCH (2005).

  25. B. List, Chem. Rev., 107, No. 12, 5413-5415 (2007).

    Article  CAS  Google Scholar 

  26. J. Song, D.-F. Chen, and L.-Z. Gong, Natl. Sci. Rev., 4, No. 3, 381-396 (2017).

    Article  CAS  Google Scholar 

  27. J. Aleman and S. Cabrera, Chem. Soc. Rev., 42, No. 2, 774-793 (2013).

    Article  CAS  PubMed  Google Scholar 

  28. E. N. Jacobsen and D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA, 107, No. 48, 20618-20619 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. D. W. C. MacMillan, Nature, 455, 304-308 (2008).

    Article  CAS  PubMed  Google Scholar 

  30. S. Zhu, S. Yu, Y. Wang, et al., Angew. Chem. Int. Ed., 49, No. 27, 4656-4660 (2010).

  31. R. Husmann, E. Sugiono, S. Mersmann, et al., Org. Lett., 13, No. 5, 1044-1047 (2011).

    Article  CAS  PubMed  Google Scholar 

  32. J. Tauber, L. A. Schwartz, and M. J. Krische, Org. Process Res. Dev., 23, No. 5, 730-736 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. D. Seebach, Chimia., 68, No. 6, 348-355 (2014).

    Article  CAS  PubMed  Google Scholar 

  34. G. Valero, X. Companyo, and R. Rios, Chem. Eur. J., 17, No. 7, 2018-2037 (2011).

    Article  CAS  PubMed  Google Scholar 

  35. P. Wuts (ed.), Greene’s Protective Groups in Organic Synthesis: Fifth Edition, John Wiley & Sons (2014).

  36. X. Han, H. Wu, W. Wang, et al., Org. Biomol. Chem., 12, No. 41, 8308-8317 (2014).

    Article  CAS  PubMed  Google Scholar 

  37. X. Dai and D. Cahard, Adv. Synth. Cat., 356, No. 6, 1317-1328 (2014).

    Article  CAS  Google Scholar 

  38. L. R. E. Pantaine, J. A. Milligan, J. K. Matsui, et al., Org. Lett., 21, No. 7, 2317-2321 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. M. Abid, M. Savolainen, S. Landge, et al., J. Fluor. Chem., 128, No. 6, 587-594 (2007).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. A. Genoni, M. Benaglia, E. Massolo, et al., Chem. Commun., 49, No. 75, 8365-8367 (2013).

    Article  CAS  Google Scholar 

  41. A. S. Kiselyov, Tetrahedron Lett., 40, No. 22., 4119-4122 (1999).

    Article  CAS  Google Scholar 

  42. S. Hayashi, H. Yorimitsu, and K. Oshima, Angew. Chem. Int. Ed., 48, No. 39, 7224-7226 (2009).

    Article  CAS  Google Scholar 

  43. D. C. Elliott, A. Marti, P. Mauleyn, et al., Chem. Eur. J., 25, No. 8, 1918-1922 (2019).

    Article  CAS  PubMed  Google Scholar 

  44. H. Amii, Y. Kishikawa, K. Kageyama, et al., J. Org. Chem., 65, No. 11, 3404-3408 (2000).

    Article  CAS  PubMed  Google Scholar 

  45. J. L. Garcia Ruano, J. Aleman, S. Catalan, et al., Angew. Chem. Int. Ed., 47, No. 41, 7941-7944 (2008).

    Article  CAS  Google Scholar 

  46. S. Fustero, C. del Pozo, S. Catalan, et al., Org. Lett., 11, No. 3, 641-644 (2009).

    Article  CAS  PubMed  Google Scholar 

  47. S. Fustero, M. Sanchez-Rosello, C. Baez, et al., Amino Acids, 41, No. 3, 559-573 (2011).

    Article  CAS  PubMed  Google Scholar 

  48. I. Aparici, M. Guerola, C. Dialer, et al., Org. Lett., 17, No. 21, 5412-5415 (2015).

    Article  CAS  PubMed  Google Scholar 

  49. J. Yang, Q.-Q. Min, Y. He, et al., Tetrahedron Lett., 52, No. 36, 4675-4677 (2011).

    Article  CAS  Google Scholar 

  50. Q.-Q. Min, C.-Y. He, H. Zhou, et al., Chem. Commun., 46, No. 42, 8029-8031.

  51. G. Huang, J. Yang, and X. Zhang, Chem. Commun., 47, No. 19, 5587-5589 (2011).

    Article  CAS  Google Scholar 

  52. F. -G. Zhang, H. Ma, Y. Zheng, et al., Tetrahedron, 68, No. 37, 7663-7669 (2012).

    Article  CAS  Google Scholar 

  53. G. Huang, Z. Yin, and X. Zhang, Chem. Eur. J., 19, No. 36, 11992-11998 (2013).

    Article  CAS  PubMed  Google Scholar 

  54. M. Abid, L. Teixeira, and B. Torok, Org.Lett., 10, No. 5, 933-935 (2008).

    Article  CAS  PubMed  Google Scholar 

  55. F. Huguenot and T. Brigaud, J. Org. Chem., 71, No. 18, 7075-7078 (2006).

    Article  CAS  PubMed  Google Scholar 

  56. D. Enders, K. Gottfried, and G. Raabe, Adv. Synth. Cat., 352, N0. 18, 3147-3152 (2010).

  57. Y. -L. Liu, T. -D. Shi, F. Zhou, et al., Org. Lett., 13, No. 15, 3826-3829 (2011).

    Article  CAS  PubMed  Google Scholar 

  58. K. Burger and N. Sewald, Synthesis, 1990, No. 2, 115-118 (1990).

    Article  Google Scholar 

  59. S. N. Osipov, A. F. Kolomiets, C. Bruneau, et al., Chem. Commun., No. 18, 2053-2054 (1998).

    Article  Google Scholar 

  60. S. N. Osipov, O. I. Artyushin, A. F. Kolomiets, et al., Eur. J. Org. Chem., 2001, No. 20, 3891-3897 (2001).

    Article  Google Scholar 

  61. M. Eckert, S. Moulin, F. Monnier, et al., Chem. Eur. J., 17, No. 34, 9456-9462 (2011).

    Article  CAS  PubMed  Google Scholar 

  62. G. T. Shchetnikov, A. S. Peregudov, and S. N. Osipov, Synlett., 2007, No. 01, 136-140 (2007).

    Article  Google Scholar 

  63. G. T. Shchetnikov, S. N. Osipov, C. Bruneau, et al., Synlett., 2008, No. 04, 578-582 (2008).

    Article  Google Scholar 

  64. D. Maisch, P. Wadhwani, S. Afonin, et al., J. Am. Chem. Soc., 131, No. 43, 15596-15597 (2009).

    Article  CAS  PubMed  Google Scholar 

  65. P. Pace, M. E. Di Francesco, C. Gardelli, et al., J. Med. Chem., 50, No. 9, 2225-2239 (2007).

    Article  CAS  PubMed  Google Scholar 

  66. K. Morisaki, M. Sawa, J. Nomaguchi, et al., Chem. Eur. J., 19, No. 26, 8417-8420 (2013).

    Article  CAS  PubMed  Google Scholar 

  67. K. Morisaki, M. Sawa, R. Yonesaki, et al., J. Am. Chem. Soc., 138, No. 19, 6194-6203 (2016).

    Article  CAS  PubMed  Google Scholar 

  68. E. Tokunaga, T. Yamamoto, E. Ito, et al., Sci. Rep., 8, No. 1, 17131 (2018).

    Article  PubMed  PubMed Central  Google Scholar 

  69. M. Crucianelli, P. Bravo, A. Arnone, et al., J. Org. Chem., 65, No. 10, 2965-2971 (2000).

    Article  CAS  PubMed  Google Scholar 

  70. P. Bravo, S. Fustero, M. Guidetti, et al., J. Org. Chem., 64, No. 23, 8731-8735 (1999).

    Article  CAS  Google Scholar 

  71. L. -H. Sun, Z. -Q. Liang, W. -Q. Jia, et al., Angew. Chem. Int. Ed., 52, No. 22, 5803-5806 (2013).

    Article  CAS  Google Scholar 

  72. L. Baragwanath, C. A. Rose, K. Zeitler, et al., J. Org. Chem., 74, No. 23, 9214-9217 (2009).

    Article  CAS  PubMed  Google Scholar 

  73. D. -L. Wang, Z. -Q. Liang, K. -Q. Chen, et al., J. Org. Chem., 80, No. 11, 5900-5905 (2015).

    Article  CAS  PubMed  Google Scholar 

  74. B. M. Trost, C. -I. Hung (Joey), and M. J. Scharf, Angew. Chem. Int. Ed., 57, No. 35, 11408-11412 (2018).

  75. N. M. Golovach, V. N. Tkachuk, V. A. Sukach, et al., Russ. J. Org. Chem., 48, No. 9, 1187-1190 (2012).

    Article  CAS  Google Scholar 

  76. J. A. Mendes, P. R. R. Costa, M. Yus, et al., Beilstein J. Org. Chem., 17, 1096-1140 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  77. P. Bravo, M. Crucianelli, B. Vergani, et al., Tetrahedron Lett., 39, No. 42, 7771-7774 (1998).

    Article  CAS  Google Scholar 

  78. A. Asensio, P. Bravo, M. Crucianelli, et al., Eur. J. Org. Chem., 2001, No. 8, 1449-1458 (2001).

    Article  Google Scholar 

  79. M. Crucianelli, F. DeAngelis, F. Lazzaro, et al., J. Fluor. Chem., 125, No. 4, 573-577 (2004).

    Article  CAS  Google Scholar 

  80. H. Xiao, Y. Huang, and F. -L. Qing, Tetrahedron Asymmetry, 21, No. 24, 2949-2955 (2010).

    Article  CAS  Google Scholar 

  81. P. Liu, Z. -J. Liu, and Wu F., Adv. Synth. Cat., 357, No. 4, 818-822 (2015).

    Article  CAS  Google Scholar 

  82. Y. Yang, Y. Huang, and F. -L. Qing, Tetrahedron Lett., 54, No. 29, 3826-3830 (2013).

    Article  CAS  Google Scholar 

  83. L. Wang, Q. Shen, and L. Lu, Chinese J. Chem., 31, No. 7, 892-900 (2013).

    Article  CAS  Google Scholar 

  84. Y. Liu, Y. Huang, and F. -L. Qing, Tetrahedron, 68, No. 25, 4955-4961 (2012).

    Article  CAS  Google Scholar 

  85. A. F. Abdel-Magid, ACS Med. Chem. Lett., 4, No. 10, 898-899 (2013).

    Google Scholar 

  86. F. Lazzaro, M. Crucianelli, F. de Angelis, et al., Tetrahedron Asymmetry, 15, No. 5, 889-893 (2004).

    Article  CAS  Google Scholar 

  87. F. Grellepois, J. Org. Chem., 78, No. 3, 1127-1137 (2013).

    Article  CAS  PubMed  Google Scholar 

  88. M. T. Robak, M. A. Herbage, and J. A. Ellman, Chem. Rev., 110, No. 6, 3600-3740 (2010).

    Article  CAS  PubMed  Google Scholar 

  89. A. Volonterio, S. Bellosta, F. Bravin, et al., Chem. Eur. J., 9, No. 18, 4510-4522 (2003).

    Article  CAS  PubMed  Google Scholar 

  90. J. Cho, K. Sawaki, S. Hanashima, et al., Chem. Commun., 50, No. 69, 9855-9858 (2014).

    Article  CAS  Google Scholar 

  91. H. Wang, X. Zhao, Y. Li, et al., Org. Lett., 8, No. 7, 1379-1381 (2006).

    Article  CAS  PubMed  Google Scholar 

  92. T. Fujisawa, Y. Kooriyama, and M. Shimizu, Tetrahedron Lett., 37, No. 22, 3881-3884 (1996).

    Article  CAS  Google Scholar 

  93. Y. -Y. Peng, P. Liu, Z. -J. Liu, et al., Tetrahedron, 74, No. 24, 3074-3080 (2018).

    Article  CAS  Google Scholar 

  94. X. -M. Yuan, J. Xu, Z. -J. Liu, et al., J. Fluor. Chem., 144, 102-107 (2012).

    Article  CAS  Google Scholar 

  95. F. Zhang, Z. -J. Liu, and J. -T. Liu, Org. Biomol. Chem., 9, No. 10, 3625-3628 (2011).

    Article  CAS  PubMed  Google Scholar 

  96. D. M. Gale and C. G. Krespan, J. Org. Chem., 33, No. 3, 1002-1008 (1968).

    Article  CAS  Google Scholar 

  97. N. D. Chkanikov, V. L. Vershinin, A. F. Kolomiets, et al., Bull. Acad. Sci. USSR Div. Chem. Sci., 36, No. 3, 624-626 (1987).

    Article  Google Scholar 

  98. M. Koos and H. S. Mosher, Tetrahedron, 49, No. 8, 1541-1546 (1993).

    Article  CAS  Google Scholar 

  99. K. Morisaki, H. Morimoto, and T. Ohshima, Chem. Commun., 53, No. 47, 6319-6322 (2017).

    Article  CAS  Google Scholar 

  100. V. A. Sukach, N. M. Golovach, V. V. Pirozhenko, et al., Tetrahedron Asymmetry, 19, No. 6, 761-764 (2008).

    Article  CAS  Google Scholar 

  101. N. M. Golovach, V. A. Sukach, and M. Vovk, Zh. Org. Pharm. Khim. [in Ukrainian], 7, No. 3, 45-48 (2009).

    CAS  Google Scholar 

  102. N. M. Golovach, V. A. Sukach, and M. V. Vovk, Russ. J. Org. Chem., 46, No. 7, 1070-1073 (2010).

    Article  CAS  Google Scholar 

  103. V. A. Sukach, N. M. Golovach, N. V. Melnichenko, et al., J. Fluor. Chem., 129, No. 12, 1180-1186 (2008).

    Article  CAS  Google Scholar 

  104. V. Sukach, S. Melnykov, S. Bertho, et al., Org. Lett., 21, No. 7, 2340-2345 (2019).

    Article  CAS  PubMed  Google Scholar 

  105. M. Sawa, K. Morisaki, Y. Kondo, et al., Chem. Eur. J., 23, No. 67, 17022-17028 (2017).

    Article  CAS  PubMed  Google Scholar 

  106. Y. V. Rassukana, Synthesis, 2011, No. 21, 3426-3428 (2011).

    Article  Google Scholar 

  107. Y. V. Rassukana, I. P. Yelenich, Y. G. Vlasenko, et al., Tetrahedron Asymmetry, 25, No. 16, 1234-1238 (2014).

    Article  CAS  Google Scholar 

  108. R. Yonesaki, Y. Kondo, W. Akkad, et al., Chem. Eur. J., 24, No. 57, 15211-15214.

  109. M. Miyagawa, M. Yoshida, Y. Kiyota, et al., Chem. Eur. J., 25, No. 22, 5677-5681 (2019).

    Article  CAS  PubMed  Google Scholar 

  110. J. Iwanejko and E. Wojaczycska, Org. Biomol. Chem., 16, No. 40, 7296-7314 (2018).

    Article  CAS  PubMed  Google Scholar 

  111. D. Saha, S. Bagchi, and A. Sharma, Chem. Heterocycl. Compd., 54, No. 3, 302-313 (2018).

    Article  CAS  Google Scholar 

  112. A. Otero, M. -J. Chapela, M. Atanassova, et al., Chem. Res. Toxicol., 24, No. 11, 1817-1829 (2011).

    Article  CAS  PubMed  Google Scholar 

  113. C. E. Stivala, E. Benoit, R. Araoz, et al., Nat. Prod. Rep., 32, No. 3, 411-435 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  114. G. S. Kauffman, G. D. Harris, R. L. Dorow, et al., Org. Lett., 2, No. 20, 3119-3121 (2000).

    Article  CAS  PubMed  Google Scholar 

  115. S. Li and J.-A. Ma, Chem. Soc. Rev., 44, No. 21, 7439-7448 (2015).

    Article  CAS  PubMed  Google Scholar 

  116. B. Jiang, J. J. Dong, Y. G. Si, et al., Adv. Synth. Cat., 350, No. 9, 1360-1366 (2008).

    Article  CAS  Google Scholar 

  117. H. Xie, Y. Zhang, S. Zhang, et al., Angew. Chem. Int. Ed., 50, No. 49, 11773-11776 (2011).

    Article  CAS  Google Scholar 

  118. F. -G. Zhang, X. -Y. Zhu, S. Li, et al., Chem. Commun., 48, No. 94, 11552 (2012).

    Article  CAS  Google Scholar 

  119. H. Xie, A. Song, X. Song, et al., Tetrahedron Lett., 54, No. 11, 1409-1411 (2013).

    Article  CAS  Google Scholar 

  120. H. -N. Yuan, S. Wang, J. Nie, et al., Angew. Chem. Int. Ed., 52, No. 14, 3869-3873 (2013).

    Article  CAS  Google Scholar 

  121. H. -N. Yuan, S. Li, J. Nie, et al., Chem. Eur. J., 19, No. 47, 15856-15860 (2013).

    Article  CAS  PubMed  Google Scholar 

  122. K .-F. Zhang, J. Nie, R. Guo, et al., Adv. Synth. Cat., 355, No. 17, 3497-3502 (2013).

  123. D. Zhou, Z. Huang, X. Yu, et al., Org. Lett., 17, No. 22, 5554-5557 (2015).

    Article  CAS  PubMed  Google Scholar 

  124. H. Asahara, Synthesis, 49, No. 15, 3366-3376 (2017).

    Article  CAS  Google Scholar 

  125. B. Zhou, C. Jiang, V. R. Gandi, et al., Chem. Eur. J., 22, No. 37, 13068-13071 (2016).

    Article  CAS  PubMed  Google Scholar 

  126. J. Dai, D. Xiong, T. Yuan, et al., Angew. Chem. Int. Ed., 56, No. 41, 12697-12701 (2017).

    Article  CAS  Google Scholar 

  127. S. Chen and K. N. Houk, J. Org. Chem., 83, No. 6, 3171-3176 (2018).

    Article  CAS  PubMed  Google Scholar 

  128. Y. Luo, K. -X. Xie, D. -F. Yue, et al., Org. Biomol. Chem., 16, No. 18, 3372-3375 (2018).

    Article  CAS  PubMed  Google Scholar 

  129. Y. Zhang, J. Nie, F. -G. Zhang, et al., J. Fluor. Chem., 208, 1-9 (2018).

    Article  CAS  Google Scholar 

  130. F. Feng, J. Li, S. Li, et al., Adv. Synth. Cat., 361, No. 18, 4222-4226 (2019).

    Article  CAS  Google Scholar 

  131. K. Singh, D. Arora, D. Falkowski, et al., Eur. J. Org. Chem., 2009, No. 19, 3258-3264 (2009).

    Article  Google Scholar 

  132. K. Singh, D. Arora, and S. Singh, Tetrahedron Lett., 48, No. 8, 1349-1352 (2007).

    Article  CAS  Google Scholar 

  133. F. Rise, D. Grace, and K. Undheim, J. Organomet. Chem., 338, No. 3, 341-346 (1988).

    Article  CAS  Google Scholar 

  134. J. J. Fox, T. L. Su, L. M. Stempel, et al., J. Org. Chem., 47, No. 6, 1081-1084 (1982).

    Article  CAS  Google Scholar 

  135. A. Katoh, Y. Omote, and C. Kashima, J. Heterocycl. Chem., 21, No. 1, 53-55 (1984).

    Article  CAS  Google Scholar 

  136. F. Rise, C. Romming, and K. Undheim, Acta Chem. Scand., 39b, 459-468 (1985).

    Article  Google Scholar 

  137. Y. Huang, F. Yang, and C. Zhu, J. Am. Chem. Soc., 127, No. 47, 16386-16387 (2005).

    Article  CAS  PubMed  Google Scholar 

  138. S. Lou, B. M. Taoka, A. Ting, et al., J. Am. Chem. Soc., 127, No. 32, 11256-11257 (2005).

    Article  CAS  PubMed  Google Scholar 

  139. X. -H. Chen, X. -Y. Xu, H. Liu, et al., J. Am. Chem. Soc., 128, No. 46, 14802-14803 (2006).

    Article  CAS  PubMed  Google Scholar 

  140. L. -Z. Gong, X. -H. Chen, and X. -Y. Xu, Chem. Eur. J., 13, No. 32, 8920-8926 (2007).

    Article  CAS  PubMed  Google Scholar 

  141. G. C. Rovnyak, S. D. Kimball, B. Beyer, et al., J. Med. Chem., 38, No. 1, 119-129 (1995).

    Article  CAS  PubMed  Google Scholar 

  142. O. P. Kleidernigg and C. O. Kappe, Tetrahedron Asymmetry, 8, No. 12, 2057-2067 (1997).

    Article  CAS  Google Scholar 

  143. V. A. Sukach, V. M. Tkachuk, V. M. Shoba, et al., Eur. J. Org. Chem., 2014, No. 7, 1452-1460 (2014).

    Article  CAS  Google Scholar 

  144. V. M. Tkachuk, Sukach V.A., K. V. Kovalchuk, et al., Org. Biomol. Chem., 13, No. 5, 1420-1428 (2015).

    Article  CAS  PubMed  Google Scholar 

  145. Sukach V. A., A. A. Resetnic, V. M. Tkachuk, et al., Eur. J. Org. Chem., 2015, No. 6, 1290-1301 (2015).

    Article  CAS  Google Scholar 

  146. M. -W. Chen, X. Mao, Y. Ji, et al., Tetrahedron Lett., 60, No. 48, 151280 (2019).

    Article  Google Scholar 

  147. G. Yang and W. Zhang, Angew. Chem. Int. Ed., 52, No. 29, 7540-7544 (2013).

    Article  CAS  Google Scholar 

  148. A. Mertens, H. Zilch, B. Koenig, et al., J. Med. Chem., 36, No. 17, 2526-2535 (1993).

    Article  CAS  PubMed  Google Scholar 

  149. S. Zhang, L. Li, Y. Hu, et al., Org. Lett., 17, No. 20, 5036-5039 (2015).

    Article  CAS  PubMed  Google Scholar 

  150. S. Zhang, L. Cha, L. Li, et al., J. Org. Chem., 81, No. 8, 3177-3187 (2016).

    Article  CAS  PubMed  Google Scholar 

  151. M. Viji, J. Sim, S. Li, et al., Adv. Synth. Cat., 360, No. 23, 4464-4469 (2018).

    Article  CAS  Google Scholar 

  152. H. Lou, Y. Wang, E. Jin, et al., J. Org. Chem., 81, No. 5, 2019-2026 (2016).

    Article  CAS  PubMed  Google Scholar 

  153. M. Patel, R. J. McHugh, B. C. Cordova, et al., Bioorg. Med. Chem. Lett., 10, No. 15, 1729-1731 (2000).

    Article  CAS  PubMed  Google Scholar 

  154. N. G. Voznesenskaia, O. I. Shmatova, V. N. Khrustalev, et al., Org. Biomol. Chem., 16, No. 38, 7004-7011 (2018).

    Article  CAS  PubMed  Google Scholar 

  155. O. I. Shmatova and V. G. Nenajdenko, Eur. J. Org. Chem., 2013, No. 28, 6397-6403 (2013).

    Article  CAS  Google Scholar 

  156. N. E. Shevchenko, K. Vlasov, V. G. Nenajdenko, et al., Tetrahedron, 67, No. 1, 69-74 (2011).

    Article  CAS  Google Scholar 

  157. O. I. Shmatova and V. G. Nenajdenko, Mendeleev Commun., 29, No. 1, 57-58 (2019).

    Article  CAS  Google Scholar 

  158. O. I. Shmatova, N. E. Shevchenko, E. S. Balenkova, et al., Eur. J. Org. Chem., 2013, No. 15, 3049-3058 (2013).

    Article  CAS  Google Scholar 

  159. O. I. Shmatova, N. E. Shevchenko, E. S. Balenkova, et al., Mendeleev Commun., 23, No. 2, 92-93 (2013).

    Article  CAS  Google Scholar 

  160. A. Rahman, E. Xie, and X. Lin, Org. Biomol. Chem., 16, No. 8, 1367-1374 (2018).

    Article  CAS  PubMed  Google Scholar 

  161. N. G. Voznesenskaia, O. I. Shmatova, M. M. Ilyin, et al., Eur. J. Org. Chem., 2019, No. 9, 1893-1903 (2019).

    Article  CAS  Google Scholar 

  162. D. Grosheva and N. Cramer, Angew. Chem. Int. Ed., 57, No. 41, 13644-13647 (2018).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. V. Vovk.

Additional information

Translated from Teoretychna ta Eksperymentalna Khimiya, Vol. 57, No. 6, pp. 333-355, November-December, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sukach, V.A., Tkachuk, V.M., Gillaizeau, I. et al. Modern Approaches to Synthetic Design of Chiral α-Tertiary Amines Based on Trifluoromethylcontaining Ketimines: A Review. Theor Exp Chem 57, 387–420 (2022). https://doi.org/10.1007/s11237-022-09710-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11237-022-09710-z

Keywords

Navigation