Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 6
198
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Stereoselective synthesis of functionalized vinyl ethers from allyl bromides activated by triethylamine

, , , , , , , & show all
Pages 705-713 | Received 10 Nov 2017, Published online: 13 Feb 2018

References

  • (a) Iftene, F.; David, G.; Boutevin, B.; Auvergne, R.; Alaaeddine, A.; Meghabar, R. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 2432–2443; (b) Kanazawa, A.; Kanaoka, S.; Aoshima, S. Macromolecules 2014, 47, 6635–6644; (c) Sugihara, S.; Kawamoto, Y.; Maeda, Y. Macromolecules 2016, 49, 1563–1574; (d) Kottisch, V.; Quentin Michaudel, Q.; Fors, B. P. J. Am. Chem. Soc. 2016, 138, 15535–15538; (e) Kanazawa, A.; Kanaoka, S.; Aoshima, S. J. Am. Chem. Soc. 2013, 135, 9330–9333.
  • (a) Tejedor, D.; Cotos, L.; García-Tellado, F. J. Org. Chem. 2013, 78, 8853–8858; (b) André, M.; Letribot, B.; Bayle, M.; Mounetou, E.; Chezal, J.-M. Tetrahedron Lett. 2012, 53, 6107–6110.
  • Oparina, L. A.; Malysheva, S. F.; Gusarova, N. K.; Vysotskaya, O. V.; Stepanov, A. V.; Belogorlova, N. A.; Albanov, A. I.; Trofimov, B. A. Synthesis 2009, 2009, 3427–3432.
  • Oparina, L. A.; Gusarova, N. K.; Vysotskaya, O. V.; Kolyvanov, N. A.; Artem’ev, A. V.; Trofimov, B. A. Synthesis 2012, 44, 2938–2946.
  • (a) Ram, R. N.; Gupta, D. K.; Soni, V. K. J. Org. Chem. 2016, 81, 1665–1674; (b) Jin, S.; Jiang, C.; Peng, X.; Shan, C.; Cui, S.; Niu, Y.; Liu, Y.; Lan, Y.; Liu, Y.; Cheng, M. Org. Lett. 2016, 18, 680–683; (c) Kim, C.-E.; Park, S.; Eom, D.; Seo, B.; Lee, P. H. Org. Lett. 2014, 16, 1900–1903; (d) Zhang, X.; Cividino, P.; Poisson, J.-F.; Shpak-Kraievskyi, P.; Laurent, M. Y.; Martel, A.; Dujardin, G.; Py, S. Org. Lett. 2014, 16, 1936–1939; (e) Murai, M.; Hosokawa, N.; Roy, D.; Takai, K. Org. Lett. 2014, 16, 4134–4137; (f) Oparina, L. A.; Vysotskaya, O. V.; Stepanov, A. V.; Ushakov, I. A.; Apartsin, K. A.; Gusarova, N. K.; Trofimov, B. A. Russ. J. Org. Chem. 2017, 53, 203–209.
  • (a) Minenkov, Y.; Occhipinti, G.; Jensen, V. R. Organometallics 2013, 32, 2099–2111; (b) Meek, S. J.; O’Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461–466.
  • (a) Gille, A.; Rehbein, J.; Hiersemann, M. Org. Lett. 2011, 13, 2122–2125; (b) Tejedor, D.; Leandro Cotos, L.; García-Tellado, F. Org. Lett. 2011, 13, 4422–4425; (c) Becker, J.; Butt, L.; von Kiedrowski, V.; Mischler, E.; Quentin, F.; Hiersemann, M. J. Org. Chem. 2014, 79, 3040–3051; (d) Vidhani, D. V.; Cran, J. W.; Krafft, M. E.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2013, 78, 2059–2073.
  • (a) Malysheva, V. F.; Gusarova, N. K.; Artem’ev, A. V.; Belogorlova, N. A.; Albanov, A. I.; Borodina, T. N.; Smirnov, V. I.; Trofimov, B. A. Eur. J. Org. Chem. 2014, 2014, 2516–2521; (b) Malysheva, S. F.; Gusarova, N. K.; Artem’ev, A. V.; Belogorlova, N. A.; Albanov, A. I.; Borodina, T. N.; Smirnov, V. I.; Trofimov, B. A. Synthesis 2014, 46, 2656–2662; (c) Oparina, L. A.; Artem’ev, A. V.; Vysotskaya, O. V.; Kolyvanov, N. A.; Bagryanskaya, Y. I.; Doronina, E. P.; Gusarova, N. K. Tetrahedron 2013, 69, 6185–6195; (d) Pahadi, N. K.; Tunge, J. A. Synlett 2009, 2009, 3135–3138.
  • Gøgsig, T. M.; Kleimark, J.; Lill, S. O. N.; Korsager, S.; Lindhardt, A. T.; Norrby, P.-O.; Skrydstrup, T. J. Am. Chem. Soc. 2012, 134, 443–452.
  • (a) Ebe, Y.; Nishimura, T. J. Am. Chem. Soc. 2015, 137, 5899–5902; (b) Iwasaki, T.; Miyata, Y.; Akimoto, R.; Fujii, Y.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2014, 136, 9260–9263.
  • Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652–1655.
  • Kundu, D.; Maity, P.; Ranu, B. C. Org. Lett. 2014, 16, 1040–1043.
  • Dehli, J. R.; Julien Legros, J.; Bolm, C. Chem. Commun. 2005, 2005, 973–986.
  • Nishimura, H.; Sasaki, M.; Seike, H.; Nakamura, M.; Watanabe, T. Org. Biomol. Chem. 2012, 10, 6432–6442.
  • Jiménez, J.; Landa, A.; Lizarraga, A.; Maestro, M.; Mielgo, A.; Oiarbide, M.; Velilla, I.; Palomo, C. J. Org. Chem. 2012, 77, 747–753.
  • Besbes, R.; Villiéras, J.; Amri, H. Indian J. Chem. Sect. B 1997, 36, 5–8.
  • Arfaoui, A.; Saâdi, F.; Nefzi, A.; Amri, H. Synth. Commun. 2015, 45, 2627–2635.
  • Arfaoui, A.; Amri, H. Tetrahedron 2009, 65, 4904–4907.
  • Khamri, S.; Amri, H. Tetrahedron 2009, 65, 4890–4893.
  • Arfaoui, A.; Béji, F.; Ben Ayed, T.; Amri, A. Synth. Commun. 2008, 38, 3717–3725.
  • (a) Su, C.; Williard, P. G. Org. Lett. 2010, 12, 5378–5381; (b) Lim, H. J.; Smith, C. R.; RajanBabu, T. V. J. Org. Chem. 2009, 74, 4565–4572.
  • Jaguar, Version 7.6; Schrodinger, LLC: New York, 2009.
  • (a) Perdrew, J. P. Phys. Rev. 1986, B33, 8822; (b) Becke, A. D. J. Chem. Phys. 1989, 90, 5622.
  • (a) Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193–218; (b) Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94, 6081–6090; (c) Frisch, J. M.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265–3269; (d) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294–301.
  • (a) Lv, L.; Zheng, S.; Cai, X.; Chen, Z.; Zhu, Q.; Liu, S. ACS Comb. Sci. 2013, 15, 183–192; (b) Zhu, Q.; Gao, L.; Chen, Z.; Zheng, S.; Shu, H.; Li, J.; Jiang, H.; Liu, S. Eur. J. Med. Chem. 2012, 54, 232–238.
  • (a) Greenwood, F. L.; Kellert, M. D.; Sedlak, J. Org. Synth. 1958, 38, 8–9; (b) Thapa, R.; Brown, J.; Balestri, T.; Taylor, R. T. Tetrahedron Lett. 2014, 55, 6743–6746.
  • CCDC 1548610 contains the supplementary crystallographic data of compound 3 for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via. http://www.ccdc.cam.ac.uk/data_request/cif.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.