Skip to main content
SpringerLink
Log in

New Syntheses and Properties of Some Axial and Helical Isomers of Organic Compounds

  • Review
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The review generalizes published data on the synthesis of atropisomeric arylimide, porphyrin, and benzimidazole derivatives, helically chiral compounds (helicenes), and axially chiral molecules.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Míguez-Lago, S. and Cid, M.M., Synthesis, 2017, vol. 49, p. 4111. doi 10.1055/s-0036-1590966

    Article  CAS  Google Scholar 

  2. Nalbandian, C.J., Hecht, D.E., and Gustafson, J.L., Synlett, 2016, vol. 27, p. 977. doi 10.1055/s-0035-1561314

    Article  CAS  Google Scholar 

  3. Porter, J., Payne, A., Whitcombe, I., de Candole, B., Ford, D., Garlish, R., Hold, A., Hutchinson, B., Trevitt, G., Turner, J., Edwards, C., Watkins, C., Davis, J., and Stubberfield, C., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 1767. doi 10.1016/j.bmcl.2009.01.071

    Article  CAS  PubMed  Google Scholar 

  4. Xing, Q., Gan, L.-S., Mou, X.-F., Wang, W., Wang, C.-Y., Weia, M.-Y., and Shao, C.-L., RSC Adv., 2016, vol. 6, p. 22653. doi 10.1039/c6ra00374e

    Article  CAS  Google Scholar 

  5. Zask, A., Murphy, J., and Ellestad, G.A., Chirality, 2013, vol. 25, p. 265. doi 10.1002/chir.22145

    Article  CAS  PubMed  Google Scholar 

  6. Wei, J., Rega, M.F., Kitada, S., Yuan, H., Zhai, D., Risbood, P., Seltzman, H.H., Twine, C.E., Reed, J.C., and Pellecchia, M., Cancer Lett., 2009, vol. 273, p. 107. doi 10.1016/j.canlet.2008.07.031

    Article  CAS  PubMed  Google Scholar 

  7. Smyth, J.E., Butler, N.M., and Keller, P.A., Nat. Prod. Rep., 2015, vol. 32, p. 1562. doi 10.1039/c4np00121d

    Article  CAS  PubMed  Google Scholar 

  8. Glushkov, R.G., Goizman, M.S., Arantseva, D.A., Demidova, N.N., Kulaeva, E.K., Zagudailova, M.B., Dmitriev, D.E., Trifilenkov, A.S., Korlyukov, A.A., Arkhipov, D.E., Suponitskii, K.Yu., Shimanovskii, N.L., Zaitsev, S.A., and Degterev, E.V., Pharm. Chem. J., 2014, vol. 48, p. 186. doi 10.1007/s11094-014-1075-x

    Article  CAS  Google Scholar 

  9. Ichikawa, M., Yokomizo, A., Itoh, M., Haginoya, N., Sugita, K., Usui, H., Terayama, K., and Kanda, A., Bioorg. Med. Chem., 2011, vol. 19, p. 5207. doi 10.1016/j.bmc.2011.07.007

    Article  CAS  PubMed  Google Scholar 

  10. Campolo, D., Gastaldi, S., Roussel, C., Bertrand, M.P., and Nechab, M., Chem. Soc. Rev., 2013, vol. 42, p. 8434. doi 10.1039/c3cs60182j

    Article  PubMed  CAS  Google Scholar 

  11. Miaskiewicz, S., Reed, J.H., Donets, P.A., Oliveira, C.C., and Cramer, N., Angew. Chem., 2018, vol. 130, p. 4103. doi 10.1002/ange.201801300

    Article  Google Scholar 

  12. Kumarasamy, E., Ayitou, A.J.-L., Vallavoju, N., Raghunathan, R., Iyer, A., Clay, A., Kandappa, S.K., and Sivaguru, J., Acc. Chem. Res., 2016, vol. 49, p. 2713. doi 10.1021/acs.accounts.6b00357

    Article  CAS  PubMed  Google Scholar 

  13. Bonne, D. and Rodriguez, J., Chem. Commun., 2017, vol. 53, p. 12385. doi 10.1039/c7cc06863h

    Article  CAS  Google Scholar 

  14. Ogasawara, M. and Watanabe, S., Synthesis, 2009, p. 1761. doi 10.1055/s-0029-1216818

    Google Scholar 

  15. Shishkina, I.N., Dotsenko, I.A., Demyanovich, V.M., Bumagin, N.A., and Zefirov, N.S., Dokl. Chem., 2012, vol. 445, p. 166. doi 10.1134/S0012500812080083

    Article  CAS  Google Scholar 

  16. Zilate, B., Castrogiovanni, A., and Sparr, C., ACS Catal., 2018, vol. 8, p. 2981. doi 10.1021/acscatal.7b04337

    Article  CAS  Google Scholar 

  17. Yangirov, T.A., Fatykhov, A.A., Sedova, E.A., Khalilov, L.M., Meshcheryakova, E.S., Ivanov, S.P., Salazkin, S.N., and Kraikin, V.A., Tetrahedron, 2019, vol. 75, p. 1282. doi 10.1016/j.tet.2019.01.043

    Article  CAS  Google Scholar 

  18. Neff, R.K. and Frantz, D.E., Tetrahedron, 2015, vol. 71, p. 7. doi 10.1016/j.tet.2014.08.030

    Article  CAS  Google Scholar 

  19. Kumarasamy, E., Raghunathan, R., Sibi, M.P., and Sivaguru, J., Chem. Rev., 2015, vol. 115, p. 11.239. doi 10.1021/acs.chemrev.5b00136

    Article  CAS  Google Scholar 

  20. Gal, J., Chirality, 2011, vol. 23, p. 647. doi 10.1002/chir.20955

    Article  CAS  PubMed  Google Scholar 

  21. Voskressensky, L.G., Golantsov, N.E., and Maharramov, A.M., Synthesis, 2016, vol. 48, p. 615. doi 10.1055/s-0035-1561503

    Article  CAS  Google Scholar 

  22. Renzi, P., Org. Biomol. Chem., 2017, vol. 15, p. 4506. doi 10.1039/c7ob00908a

    Article  CAS  PubMed  Google Scholar 

  23. Clayden, J., Chem. Commun., 2004, p. 127. doi 10.1039/B307976G

    Google Scholar 

  24. Rais, E., Florke, U., and Wilhelm, R., Synthesis, 2017, vol. 49, p. 2852. doi 10.1055/s-0036-1588849

    Article  CAS  Google Scholar 

  25. Stolić, I., Molčanov, K., Kovačević, G., Kojić-Prodić, B., and Bajić, M., Struct. Chem., 2012, vol. 23, p. 425. doi 10.1007/s11224-011-9885-x

    Article  CAS  Google Scholar 

  26. Walton, I.M., Cox, J.M., Benson, C.A., Patel, D.G., Chen, Y.-S., and Benedict, J.B., New J. Chem., 2016, vol. 40, p. 101. doi 10.1039/c5nj01718a

    Article  CAS  Google Scholar 

  27. Ruiz, N., Aaliti, A., Forniés-Cámer, J., Ruiz, A., Claver, C., Cardin, C.J., Fabbri, D., and Gladiali, S., J. Organomet. Chem., 1997, vols. 545–546, p. 79. doi 10.1016/S0022-328X(97)00151-4

    Article  Google Scholar 

  28. Gladiali, S., Fabbri, D., Kollar, L., Claver, C., Ruiz, N., Alvarez-Larena, A., and Piniella, J.F., Eur. J. Inorg. Chem., 1998, p. 113. doi 10.1002/(SICI)1099-0682(199801)1998:1

    Google Scholar 

  29. Ruiz, N., Rio, I.D., Jimenez, J.L., Claver, C., Fornies-Camer, J., Cardin, C.C.J., and Gladiali, S., J. Mol. Catal. A: Chem., 1999, vol. 143, p. 171. doi 10.1016/S1381-1169(98)00383-5

    Article  CAS  Google Scholar 

  30. Wu, G., Qi, X., Mo, X., Yu, G., Wang, Q., Zhu, T., Gu, Q., Liu, M., Li, J., and Li, D., Eur. J. Med. Chem., 2018, vol. 148, p. 268. doi 10.1016/j.ejmech.2018.02.041

    Article  CAS  PubMed  Google Scholar 

  31. Saepua, S., Kornsakulkarn, J., Somyong, W., Laksanacharoen, P., Isaka, M., and Thongpanchang, C., Tetrahedron, 2018, vol. 74, p. 859. doi 10.1016/j.tet.2018.01.004

    Article  CAS  Google Scholar 

  32. Cao, N., Chen, Y., Ma, X., Zeng, K., Zhao, M., Tu, P., Li, J., and Jiang, Y., Phytochemistry, 2018, vol. 151, p. 1. doi 10.1016/j.phytochem.2018.03.009

    Article  PubMed  CAS  Google Scholar 

  33. Breazzano, S.P. and Boger, D.L., J. Am. Chem. Soc., 2011, vol. 133, p. 18.495. doi 10.1021/ja208570q

    Article  CAS  Google Scholar 

  34. Anyika, M., Gholami, H., Ashtekar, K.D., Acho, R., and Borhan, B., J. Am. Chem. Soc., 2014, vol. 136, p. 550. doi 10.1021/ja408317b

    Article  CAS  PubMed  Google Scholar 

  35. Xu, Z., Wang, Q., and Zhu, J., J. Am. Chem. Soc., 2013, vol. 135, p. 19.127. doi 10.1021/ja4115192

    Google Scholar 

  36. Clayden, J., Angew. Chem., Int. Ed. Engl., 1997, vol. 36, p. 949. doi 10.1002/anie.199709491

    Article  CAS  Google Scholar 

  37. Quinonero, O., Bressy, C., and Bugaut, X., Angew. Chem., 2014, vol. 126, p. 11.039. doi 10.1002/ange.201406263

    Article  Google Scholar 

  38. He, J., Kimani, F.W., and Jewett, J.C., Synlett, 2017, vol. 28, p. 1767. doi 10.1055/s-0036-1588797

    Article  CAS  Google Scholar 

  39. Nishio, S., Somete, T., Sugie, A., Kobayashi, T., Yaita, T., and Mori, A., Org. Lett., 2012, vol. 14, p. 2476. doi 10.1021/ol300755y

    Article  CAS  PubMed  Google Scholar 

  40. Zhao, T.S.N., Zhao, J., and Szabo, K.J., Org. Lett., 2015, vol. 17, p. 2290. doi 10.1021/acs.orglett.5b01048

    Article  CAS  PubMed  Google Scholar 

  41. Teply, F., Stara, I.G., Stary, I., Kollarovic, A., Syaman, D., Vyskocil, S., and Fiedler, P., J. Org. Chem., 2003, vol. 68, p. 5193. doi 10.1021/jo034369t

    Article  CAS  PubMed  Google Scholar 

  42. Katz, T.J., Angew. Chem., Int. Ed., 2000, vol. 39, p. 1921. doi 10.1002/1521-3773(20000602)39:11

    Article  CAS  Google Scholar 

  43. Shahabuddin, M., Miah, M.J., Iimura, K., Kimura, T., and Karikomi, M., Tetrahedron Lett., 2017, vol. 58, p. 1334. doi 10.1016/j.tetlet.2017.02.057

    Article  CAS  Google Scholar 

  44. Shahabuddin, M., Akutsu, A., Kimura, T., and Karikomi, M., Synthesis, 2017, vol. 49, p. 1547. doi 10.1055/s-0036-1588668

    Article  CAS  Google Scholar 

  45. Rybáček, J., Huerta-Angeles, G., Kollárovič, A., Stara, I.G., Stary, I., Rahe, P., Nimmrich, M., and Kuhnle, A., Eur. J. Org. Chem., 2011, p. 853. doi 10.1002/ejoc.201001110

    Google Scholar 

  46. Fujikawa, T., Segawa, Y., and Itami, K., J. Org. Chem., 2017, vol. 82, p. 7745. doi 10.1021/acs.joc.7b01540

    Article  CAS  PubMed  Google Scholar 

  47. Amatore, M. and Aubert, C., Eur. J. Org. Chem., 2015, p. 265. doi 10.1002/ejoc.201403012

    Google Scholar 

  48. Duwald, R., Pascal, S., Bosson, J., Grass, S., Besnard, C., Bergi, T., and Lacour, J., Chem. Eur. J., 2017, vol. 23, p. 13.596. doi 10.1002/chem.201703441

    Article  CAS  Google Scholar 

  49. Yang, W., Longhi, G., Abbate, S., Lucotti, A., Tommasini, M., Villani, C., Catalano, V.J., Lykhin, A.O., Varganov, S.A., and Chalifoux, W.A., J. Am. Chem. Soc., 2017, vol. 139, p. 13.102. doi 10.1021/jacs.7b06848

    Google Scholar 

  50. Liu, Y., Vignon, S.A., Zhang, X., Houk, K.N., and Stoddart, J.F., Chem. Commun., 2005, p. 3927. doi 10.1039/b507679j

    Google Scholar 

  51. Han, J.-W., Li, X., and Wong, H.N.C., Chem. Rec., 2015, vol. 15, p. 107. doi 10.1002/tcr.201402047

    Article  CAS  PubMed  Google Scholar 

  52. Hitosugi, S., Nakanishi, W., Yamasaki, T., and Isobe, H., Nat. Commun., 2011, vol. 2, p. 492. doi 10.1038/ncomms1505

    Article  CAS  Google Scholar 

  53. Hitosugi, S., Nakanishi, W., and Isobe, H., Chem. Asian J., 2012, vol. 7, p. 1465. doi 10.1002/asia.201200187

    Article  Google Scholar 

  54. Pascal, R.A., Jr., Dudnikov, A., Love, L.A., Geng, X., Dougherty, K.J., Mague, J.T., Kraml, C.M., and Byrne, N., Eur. J. Org. Chem., 2017, p. 4194. doi 10.1002/ejoc.201700732

    Google Scholar 

  55. Zhang, G.-W., Li, P.-F., Meng, Z., Wang, H.-X., Han, Y., and Chen, C.-F., Angew. Chem., Int. Ed., 2016, vol. 55, p. 5304. doi 10.1002/anie.201600911

    Article  CAS  Google Scholar 

  56. Tokoro, Y., Ohtsuka, N., Kusakabe, A., and Fukuzawa, S., Eur. J. Org. Chem., 2017, p. 2353. doi 10.1002/ejoc.201700102

    Google Scholar 

  57. Baker, R.W., Hockless, D.C.R., Pocock, G.R., Sargent, M.V., Skelton, B.W., Sobolev, A.N., Twiss (née Stanojevic), E., and White, A.H., J. Chem. Soc., Perkin Trans. 1, 1995, p. 2615. doi 10.1039/P19950002615

    Google Scholar 

  58. Clayden, J., Kubinski, P.M., Sammiceli, F., Helliwell, M., and Diorazio, L., Tetrahedron, 2004, vol. 60, p. 4387. doi 10.1016/j.tet.2004.01.099

    Article  CAS  Google Scholar 

  59. Thaler, T., Geittner, F., and Knochel, P., Synlett, 2007, p. 2655. doi 10.1055/s-2007-991047

    Google Scholar 

  60. Bhayana, B., J. Org. Chem., 2013, vol. 78, p. 6758. doi 10.1021/jo400782e

    Article  CAS  PubMed  Google Scholar 

  61. Kokan, Z. and Chmielewski, M.J., J. Am. Chem. Soc., 2018, vol. 140, p. 16.010. doi 10.1021/jacs.8b08689

    Article  CAS  Google Scholar 

  62. Li, W., Zhou, S.-P., Jin, Y.-P., Huang, X.-F., Zhou, W., Han, M., Yu, Y., Yan, K.-J., Li, S.-M., Ma, X.-H., Guo, Z.-X., Zhu, Y.-H., and Sun, H., Fitoterapia, 2014, vol. 98, p. 248. doi 10.1016/j.fitote.2014.08.018

    Article  CAS  PubMed  Google Scholar 

  63. Stephens, P.J., Aamouche, A., Devlin, F.J., Superchi, S., Donnoli, M.I., and Rosini, C., J. Org. Chem., 2001, vol. 66, p. 3671. doi 10.1021/jo001403k

    Article  CAS  PubMed  Google Scholar 

  64. Takahashi, H., Wakamatsu, S., Tabata, H., Oshitari, T., Harada, A., Inoue, K., and Natsugari, H., Org. Lett., 2011, vol. 13, p. 760. doi 10.1021/ol103008d

    Article  CAS  PubMed  Google Scholar 

  65. Wakamatsu, S., Takahashi, Y., Oshitari, T., Tani, N., Azumaya, I., Katsumoto, Y., Tanaka, T., Hosoi, S., Natsugari, H., and Takahashi, H., Chem. Eur. J., 2013, vol. 19, p. 7056. doi 10.1002/chem.201300064

    Article  CAS  PubMed  Google Scholar 

  66. Takahashi, Y., Wakamatsu, S., Tabata, H., Oshitari, T., and Takahashi, H., Synthesis, 2015, vol. 47, p. 2125. doi 10.1055/s-0034-1380537

    Article  CAS  Google Scholar 

  67. Tabata, H., Kayama, S., Takahashi, Y., Tani, N., Wakamatsu, S., Tasaka, T., Oshitari, T., Natsugari, H., and Takahashi, H., Org. Lett., 2014, vol. 16, p. 1514. doi 10.1021/ol500417t

    Article  CAS  PubMed  Google Scholar 

  68. Sigrist, R. and Hansen, H.-J., Helv. Chim. Acta, 2014, vol. 97, p. 1165. doi 10.1002/hlca.201400079

    Article  CAS  Google Scholar 

  69. Guo, R., Li, K.-N., Liu, B., Zhu, H.-J., Fan, Y.-M., and Gong, L.-Z., Chem. Commun., 2014, vol. 50, p. 5451. doi 10.1039/c4cc01397b

    Article  CAS  Google Scholar 

  70. Freedman, T.B., Cao, X.-L., Dukor, R.K., and Nafie, L.A., Chirality, 2003, vol. 15, p. 743. doi 10.1002/chir.10287

    Article  CAS  PubMed  Google Scholar 

  71. Banerjee, S., Riggs, B.E., Zakharov, L.N., and Blakemore, P.R., Synthesis, 2015, vol. 47, p. 4008. doi 10.1055/s-0035-1560640

    Article  CAS  Google Scholar 

  72. Smith, C.R., Mans, D.J., and RajanBabu, T.V., Org. Synth., 2008, vol. 85, p. 238. doi 10.15227/orgsyn.085.0238

    Article  CAS  PubMed  Google Scholar 

  73. Liu, Z., Cao, Z., and Du, H., Org. Biomol. Chem., 2011, vol. 9, p. 5369. doi 10.1039/C1OB05803G

    Article  CAS  PubMed  Google Scholar 

  74. Barbero, M., Cadamuro, S., Dughera, S., and Torregrossa, R., Org. Biomol. Chem., 2014, vol. 12, p. 3902. doi 10.1039/c4ob00552j

    Article  CAS  PubMed  Google Scholar 

  75. Bai, X.-F., Deng, W.-H., Xu, Z., Li, F.-W., Deng, Y., Xia, C.-G., and Xu, L.-W., Chem. Asian J., 2014, vol. 9, p. 1108. doi 10.1002/asia.201301727

    Article  CAS  PubMed  Google Scholar 

  76. Betson, M.S., Clayden, J., Helliwell, M., Johnson, P., Lai, L.W., Pink, J.H., Stimson, C.C., Vassiliou, N., Westlund, N., Yasin, S.A., and Youssef, L.H., Org. Biomol. Chem., 2006, vol. 4, p. 424. doi 10.1039/b514557k

    Article  CAS  PubMed  Google Scholar 

  77. Takahashi, I., Suzuki, Y., and Kitagawa, O., Org. Prep. Proced. Int., 2014, vol. 46, p. 1. doi 10.1080/00304948.2014.866467

    Article  CAS  Google Scholar 

  78. Goto, H., Sudoh, M., Kawamoto, K., Sugimoto, H., and Inoue, S., Chirality, 2012, vol. 24, p. 867. doi 10.1002/chir.22093

    Article  CAS  PubMed  Google Scholar 

  79. Rasberry, R.D. and Shimizu, K.D., Org. Biomol. Chem., 2009, vol. 7, p. 3899. doi 10.1039/b909567e

    Article  CAS  PubMed  Google Scholar 

  80. Degenhardt, C.F. III, Lavin, J.M., Smith, M.D., and Shimizu, K.D., Org. Lett., 2005, vol. 7, p. 4079. doi 10.1021/ol051325t

    Article  CAS  PubMed  Google Scholar 

  81. Degenhardt, C.F. III, Shortell, D.B., Adams, R.D., and Shimizu, K.D., Chem. Commun., 2000, p. 929. doi 10.1039/b002085k

    Google Scholar 

  82. Wang, C. and Matile, S., Chem. Eur. J., 2017, vol. 23, p. 11.955. doi 10.1002/chem.201702672

    CAS  Google Scholar 

  83. Chong, Y.S., Dial, B.E., Burns, W.G., and Shimizu, K.D., Chem. Commun., 2012, vol. 48, p. 1296. doi 10.1039/C2CC16511B

    Article  CAS  Google Scholar 

  84. Chong, Y.S., Smith, M.D., and Shimizu, K.D., J. Am. Chem. Soc., 2001, vol. 123, p. 7463. doi 10.1021/ja0158713

    Article  CAS  PubMed  Google Scholar 

  85. Ponomarev, G.V., Chem. Heterocycl. Compd., 1997, vol. 33, p. 1127. doi 10.1007/BF02290864

    Article  CAS  Google Scholar 

  86. Belykh, D.V., Tarabukina, I.S., Gruzdev, I.V., and Kuchin, A.V., Russ. J. Org. Chem., 2009, vol. 45, p. 452. doi 10.1134/S1070428009030191

    Article  CAS  Google Scholar 

  87. Belykh, D.V., Khudaeva, I.S., Buravlev, E.V., Chukicheva, I.Yu., Shevchenko, O.G., and Kutchin, A.V., Russ. J. Org. Chem., 2017, vol. 53, p. 610. doi 10.1134/S1070428017040182

    Article  CAS  Google Scholar 

  88. Simonov, O.R., Zaitseva, S.V., and Koifman, O.I., Russ. J. Gen. Chem., 2008, vol. 78, p. 1260. doi 10.1134/S1070363208060285

    Article  CAS  Google Scholar 

  89. Ivanova, Yu.B., Toldina, O.V., Sheinin, V.B., and Mamardashvili, N.Zh., Russ. J. Org. Chem., 2007, vol. 43, p. 1397. doi 10.1134/S1070428007090230

    Article  CAS  Google Scholar 

  90. Guseva, G.B., Dudina, N.A., Antina, E.V., V’yugin, A.I., and Semeikin, A.S., Russ. J. Gen. Chem., 2008, vol. 78, p. 1215. doi 10.1134/S1070363208060200

    Article  CAS  Google Scholar 

  91. Plieger, P.G., Burrell, A.K., Jameson, G.B., and Officer, D.L., Dalton Trans., 2004, p. 319. doi 10.1039/b312898a

    Google Scholar 

  92. Poriel, C., Ferrand, Y., Le Maux, P., and Simonneaux, G., Synlett, 2003, p. 71. doi 10.1055/s-2003-36231

    Google Scholar 

  93. Collman, J.P. and Decreáu, R.A., Org. Lett., 2005, vol. 7, p. 975. doi 10.1021/ol048185s

    Article  CAS  PubMed  Google Scholar 

  94. Schlundt, S., Bauer, W., and Hirsch, A., Chem. Eur. J., 2015, vol. 21, p. 12.421. doi 10.1002/chem.201501254

    Article  CAS  Google Scholar 

  95. Ruppert, M., Spänig, F., Wielopolski, M., Jäger, C.M., Bauer, W., Clark, T., Hirsch, A., and Guldi, D.M., Chem. Eur. J., 2010, vol. 16, p. 10.797. doi 10.1002/chem.201000760

    Article  CAS  Google Scholar 

  96. Wollman, T.G. and Hendrickson, D.N., Inorg. Chem., 1977, vol. 16, p. 3079. doi 10.1021/ic50178a019

    Article  Google Scholar 

  97. Venkataraman, S., Prabhuraja, V., Mishra, R., Kumar, R., Chandrashekar, T.K., Teng, W., and Senge, K.R., Indian J. Chem., Sect. A, 2003, vol. 42, p. 2191.

    Google Scholar 

  98. Gordienko, O.V., Tolmachev, A.A., Kornilov, M.Yu., Zubatyuk, R.I., and Shishkin, O.V., Russ. J. Org. Chem., 2011, vol. 47, p. 83. doi 10.1134/S107042801101009X

    Article  CAS  Google Scholar 

  99. Janíkova, K., Jedinak, L., Volna, T., and Canka, P., Tetrahedron, 2018, vol. 74, p. 606. doi 10.1016/j.tet.2017.12.042

    Article  CAS  Google Scholar 

  100. Zhai, F. and Jordan, R.F., Organometallics, 2017, vol. 36, p. 2784. doi 10.1021/acs.organomet.7b00283

    Article  CAS  Google Scholar 

  101. Rajan, B. and Bedekar, A.V., Synlett, 2017, vol. 28, p. 2262. doi 10.1055/s-0036-1590820

    Article  CAS  Google Scholar 

  102. Jakubec, M., Beranek, T., Jakubik, P., Sykora, J., Žádný, J., Církva, V., and Storch, J., J. Org. Chem., 2018, vol. 83, p. 3607. doi 10.1021/acs.joc.7b03234

    Article  CAS  PubMed  Google Scholar 

  103. Ravat, P., Hinkelmann, R., Steinebrunner, D., Prescimone, A., Bodoky, I., and Juriček, M., Org. Lett., 2017, vol. 19, p. 3707. doi 10.1021/acs.orglett.7b01461

    Article  CAS  PubMed  Google Scholar 

  104. Hellou, N., Macé, A., Martin, C., Dorcet, V., Roisnel, T., Jean, M., Vanthuyne, N., Berrée, F., Carboni, B., and Crassous, J., J. Org. Chem., 2018, vol. 83, p. 484. doi 10.1021/acs.joc.7b02619

    Article  CAS  PubMed  Google Scholar 

  105. Nakakuki, Y., Hirose, T., Sotome, H., Miyasaka, H., and Matsuda, K., J. Am. Chem. Soc., 2018, vol. 140, p. 4317. doi 10.1021/jacs.7b13412

    Article  CAS  PubMed  Google Scholar 

  106. Tsujihara, T., Zhou, D.-Y., Suzuki, T., Tamura, S., and Kawano, T., Org. Lett., 2017, vol. 19, p. 3311. doi 10.1021/acs.orglett.7b01470

    Article  CAS  PubMed  Google Scholar 

  107. Faigl, F., Erdelyi, Z., Nyerges, M., and Matarovolgyi, B., Tetrahedron: Asymmetry, 2015, vol. 26, p. 738. doi 10.1016/j.tetasy.2015.06.004

    Article  CAS  Google Scholar 

  108. Morimoto, Y., Shimizu, S., Mokuya, A., Ototake, N., Saito, A., and Kitagawa, O., Tetrahedron, 2016, vol. 72, p. 5221. doi 10.1016/j.tet.2015.05.001

    Article  CAS  Google Scholar 

  109. Liu, Y., Feng, X., and Du, H., Org. Biomol. Chem., 2015, vol. 13, p. 125. doi 10.1039/c4ob01087f

    Article  CAS  PubMed  Google Scholar 

  110. Miyaji, R., Wada, Y., Matsumoto, A., Asano, K., and Matsubara, S., Beilstein J. Org. Chem., 2017, vol. 13, p. 1518. doi 10.3762/bjoc.13.151

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  111. Di Iorio, N., Soprani, L., Crotti, S., Marotta, E., Mazzanti, A., Righi, P., and Bencivenni, G., Synthesis, 2017, vol. 49, p. 1519. doi 10.1055/s-0036-1588408

    Article  CAS  Google Scholar 

  112. Zhang, J.-W., Xu, J.-H., Cheng, D.-J., Shi, C., Liu, X.-Y., and Tan, B., Nat. Commun., 2016, vol. 7, p. 1. doi 10.1038/ncomms10677

    Google Scholar 

  113. Brandes, S., Bella, M., Kjærsgaard, A., and Jørgensen, K.A., Angew. Chem., 2006, vol. 118, p. 1165. doi 10.1002/ange.200503042

    Article  Google Scholar 

  114. Islas-Gonzalez, G., Bois-Choussy, M., and Zhu, J., Org. Biomol. Chem., 2003, vol. 1, p. 30. doi 10.1039/b208905j

    Article  CAS  PubMed  Google Scholar 

  115. Shindoh, N., Takemoto, Y., and Takasu, K., Chem. Eur. J., 2009, vol. 15, p. 7026. doi 10.1002/chem.200901103

    Article  CAS  PubMed  Google Scholar 

  116. Ototake, N., Taguchi, T., and Kitagawa, O., Tetrahedron Lett., 2008, vol. 49, p. 5458. doi 10.1016/j.tetlet.2008.07.017

    Article  CAS  Google Scholar 

  117. Arthur, R.J., Coogan, M.P., Casadesus, M., Haigh, R., Headspith, D.A., Francesconi, M.G., and Laye, R.H., CrystEngComm, 2009, vol. 11, p. 610. doi 10.1039/b814424a

    Article  CAS  Google Scholar 

  118. Skladchikov, D.A., Buranbaeva, R.S., Fatykhov, A.A., Ivanov, S.P., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 1550. doi 10.1134/S1070428012120093

    Article  CAS  Google Scholar 

  119. Almeida, C., Hemberger, Y., Schmitt, S.M., Bouhired, S., Natesan, L., Kehraus, S., Dimas, K., Gutschow, M., Bringmann, G., and Konig, G.M., Chem. Eur. J., 2012, vol. 18, p. 8827. doi 10.1002/chem.201103278

    Article  CAS  PubMed  Google Scholar 

  120. Min, C., Lin, Y., and Seidel, D., Angew. Chem., Int. Ed., 2017, vol. 56, p. 15.353. doi 10.1002/anie.201709182

    Article  CAS  Google Scholar 

  121. Skladchikov, D.A., Fatykhov, A.A., and Gataullin, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 383. doi 10.1134/s1070428012030086

    Article  CAS  Google Scholar 

  122. Skladchikov, D.A., Suponitskii, K.Yu., and Gataullin, R.R., Russ. J. Org. Chem., 2013, vol. 49, p. 1486. doi 10.1134/S107042801310014X

    Article  CAS  Google Scholar 

  123. Skladchikov, D.A. and Gataullin, R.R., Russ. J. Gen. Chem., 2013, vol. 83, p. 368. doi 10.1134/S1070363213020217

    Article  CAS  Google Scholar 

  124. Drawanz, B.B., Zimmer, G.C., Rodrigues, L.V., Nörnberg, A.B., Hörner, M., Frizzo, C.P., and Cunico, W., Synthesis, 2017, vol. 49, p. 5167. doi 10.1055/s-0036-1590866

    Article  CAS  Google Scholar 

  125. Mandel, J., Pan, X., Hay, E.B., Geib, S.J., Wilcox, C.S., and Curran, D.P., J. Org. Chem., 2013, vol. 78, p. 4083. doi 10.1021/jo400385t

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  126. Adler, T., Bonjoch, J., Clayden, J., Font-Bardia, M., Pickworth, M., Solans, X., Sole, D., and Vallverdu, L., Org. Biomol. Chem., 2005, vol. 3, p. 3173. doi 10.1039/b507202f

    Article  CAS  PubMed  Google Scholar 

  127. Hughes, A.D., Price, D.A., and Simpkins, N.S., J. Chem. Soc., Perkin Trans. 1, 1999, p. 1295. doi 10.1039/A901154D

    Google Scholar 

  128. Clay, A., Kumarasamy, E., Ayitou, A.J.-L., and Sivaguru, J., Chem. Lett., 2014, vol. 43, p. 1816. doi 10.1246/cl.140819

    Article  CAS  Google Scholar 

  129. Raghunathan, R., Kumarasamy, E., Iyer, A., Ugrinov, A., and Sivaguru, J., Chem. Commun., 2013, vol. 49, p. 8713. doi 10.1039/C3CC44281K

    Article  CAS  Google Scholar 

  130. Matsuoka, M., Goto, M., Wzorek, A., Soloshonok, V.A., and Kitagawa, O., Org. Lett., 2017, vol. 19, p. 2650. doi 10.1021/acs.orglett.7b00998

    Article  CAS  PubMed  Google Scholar 

  131. Gataullin, R.R., Russ. J. Org. Chem., 2018, vol. 54, p. 1. doi 10.1134/S1070428018010013

    Article  CAS  Google Scholar 

  132. Hasegawa, F., Kawamura, K., Tsuchikawa, H., and Murata, M., Bioorg. Med. Chem., 2017, vol. 25, p. 4506. doi 10.1016/j.bmc.2017.06.042

    Article  CAS  PubMed  Google Scholar 

  133. Sakhautdinov, I.M., Malikova, R.N., Ishbaeva, S.M., Lobov, A.N., Spirikhin, L.V., and Yunusov, M.S., Chem. Nat. Compd., 2018, vol. 54, p. 365. doi 10.1007/s10600-018-2348-5

    Article  CAS  Google Scholar 

  134. Yao, G., Ye, M., Huang, R., Li, Y., Zhu, Y., Pan, Y., Liao, Z.-X., and Wang, H., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6755. doi 10.1016/j.bmcl.2013.10.028

    Article  CAS  PubMed  Google Scholar 

  135. Yao, G., Li, Y., Zhu, Y., Pan, Y., Huang, R., Wang, H., and Liao, Z.-X., New J. Chem., 2014, vol. 38, p. 693. doi 10.1039/c3nj01194a

    Article  CAS  Google Scholar 

  136. Sakamoto, M., Yagishita, F., Ando, M., Sasahara, Y., Kamataki, N., Ohta, M., Mino, T., Kasashima, Y., and Fujita, T., Org. Biomol. Chem., 2010, vol. 8, p. 5418. doi 10.1039/c0ob00262c

    Article  CAS  PubMed  Google Scholar 

  137. Moore, T.W., Sana, K., Yan, D., Thepchatri, P., Ndungu, J.M., Saindane, M.T., Lockwood, M.A., Natchus, M.G., Liotta, D.C., Plemper, R.K., Snyder, J.P., and Sun, A., Beilstein J. Org. Chem., 2013, vol. 9, p. 197. doi 10.3762/bjoc.9.23

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  138. Grimmer, C., Moore, T.W., Padwa, A., Prussia, A., Wells, G., Wu, S., Sun, A., and Snyder, J.P., J. Chem. Inf. Model., 2014, vol. 54, p. 2214. doi 10.1021/ci500204

    Article  CAS  PubMed  Google Scholar 

  139. Li, W.S., Wu, J., Li, J., Satyanandamurty, T., Shen, L., and Bringmann, G., Org. Lett., 2017, vol. 19, p. 182. doi 10.1021/acs.orglett.6b03479

    Article  CAS  PubMed  Google Scholar 

  140. Baunach, M., Ding, L., Bruhn, T., Bringmann, G., and Hertweck, C., Angew. Chem., 2013, vol. 125, p. 9210. doi 10.1002/ange.201303733

    Article  Google Scholar 

  141. Clayden, J., Stimson, C.C., Helliwell, M., and Keenan, M., Synlett, 2006, p. 873. doi 10.1055/s-2006-939043

    Google Scholar 

  142. Clayden, J., Turner, H., Helliwell, M., and Moir, E., J. Org. Chem., 2008, vol. 73, p. 4415. doi 10.1021/jo702706c

    Article  CAS  PubMed  Google Scholar 

  143. Bai, X.-F., Song, T., Xu, Z., Xia, C.-G., Huang, W.-S., and Xu, L.-W., Angew. Chem., Int. Ed., 2015, vol. 54, p. 5255. doi 10.1002/anie.201501100

    Article  CAS  Google Scholar 

  144. Clayden, J., Mitjans, D., and Youssef, L.H., J. Am. Chem. Soc., 2002, vol. 124, p. 5266. doi 10.1021/ja017702o

    Article  CAS  PubMed  Google Scholar 

  145. Clayden, J., Tetrahedron Lett., 1996, vol. 37, p. 5577. doi 10.1016/0040-4039(96)01129-X

    Article  CAS  Google Scholar 

  146. Albert, J.S., Ohnmacht, C., Bernstein, P.R., Rumsey, W.L., Aharony, D., Alelyunas, Y., Russell, D.J., Potts, W., Sherwood, S.A., Shen, L., Dedinas, R.F., Palmer, W.E., and Russell, K., J. Med. Chem., 2004, vol. 47, p. 519. doi 10.1021/jm030197g

    Article  CAS  PubMed  Google Scholar 

  147. Guile, S.D., Bantick, J.R., Cooper, M.E., Donald, D.K., Eyssade, C., Ingall, A.H., Lewis, R.J., Martin, B.P., Mohammed, R.T., Potter, T.J., Reynolds, R.H., St- Gallay, S.A., and Wright, A.D., J. Med. Chem., 2007, vol. 50, p. 254. doi 10.1021/jm060995h

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This review was written in the framework of state assignment no. AAAA-A19-119011790021-4.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia

    R. R. Gataullin

Authors
  1. R. R. Gataullin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. R. Gataullin.

Ethics declarations

The author declares the absence of conflict of interests.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1321–1351.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gataullin, R.R. New Syntheses and Properties of Some Axial and Helical Isomers of Organic Compounds. Russ J Org Chem 55, 1247–1274 (2019). https://doi.org/10.1134/S107042801909001X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801909001X

Keywords

Search

Navigation