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Four-component couplingvia a sequence of threeAd E reactions involving arenesulfenyl chloride, two alkyl vinyl ether units, and silicon-containing π-donors as a method for the synthesis of polyfunctional compounds

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

A protocol for the synthesis of polyfunctional compounds by a Lewis acid initiated tandem sequence of threeAd E reactions of sulfur-containing electrophiles with two alkyl vinyl ether units and silicon containing π-donors is proposed.

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References

  1. W. A. Smit, R. Caple, and I. P. Smoliakova,Chem. Rev., 1994,94, 2359.

    Article  CAS  Google Scholar 

  2. M. A. Ibragimov, W. A. Smit, A. S. Gybin, and M. Z. Krimer,Izv. Akad. Nauk, Ser. Khim., 1983, 161 [Bull. Acad., Sci. USSR, Div. Chem. Sci., 1983,32, 137 (Engl. Transl.)].

    Google Scholar 

  3. M. A. Ibragimov, O. V. Lubinskaya, and W. A. Smit,Izv. Akad. Nauk, Ser. Khim., 1983, 1839 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983,32, 1665 (Engl. Transl.)].

    Google Scholar 

  4. M. A. Ibragimov, M. I. Lazareva, and W. A. Smit,Synthesis, 1985, 880.

  5. M. A. Ibragimov, W. A. Smit, and M. I. Lazareva,Izv. Akad. Nauk, Ser. Khim., 1985, 392 [Bull. Acad., Sci. USSR, Div. Chem. Sci., 1985,34, 359 (Engl. Transl.)].

    Google Scholar 

  6. W. A. Smit and I. P. Smoliakova,Izv. Akad. Nauk, Ser. Khim., 1985, 485 [Bull. Acad., Sci. USSR, Div. Chem. Sci., 1985,34, 443 (Engl. Transl.)].

  7. I. P. Smoliakova, W. A. Smit, and A. I. LutsenkoIzv. Akad. Nauk, Ser. Khim., 1987, 119 [Bull. Acad., Sci. USSR, Div. Chem. Sci., 1987,36, 104 (Engl. Transl.)].

  8. I. P. Smoliakova, W. A. Smit, and B. D. Osinov,Tetrahedron Lett., 1991,32, 2601.

    Article  Google Scholar 

  9. I. P. Smoliakova, Ph. D. (Chem.) Thesis, Institute of Organic Chemistry, USSR Akad. Sci., Moscow, 1989 (in Russian).

  10. A. Hayford, M. Lovdahl, M. I. Lazareva, Yu. K. Kryschenko, T. Johnson, A. D. Dilman, I. P. Smoliakova, R. Caple, and W. A. Smit,Mendeleev Commun., 1997, 48.

  11. P. A. Grieco, J. J. Nunes, and H. D. Gaul,J. Am. Chem. Soc., 1990,112, 4595.

    Article  CAS  Google Scholar 

  12. M. T. Reetz, B. Raguse, C. F. Marth, H. M. Hugel, T. Bach, and D. N. A. Fox,Tetrahedron, 1992,48, 5731.

    CAS  Google Scholar 

  13. A. B. Borisov, I. V. Bodrikov, G. N. Borisova, V. K. Bel'sky, W. A. Smit, and A. I. Lutsenko,Mendeleev Commun., 1996, 52.

  14. M. Santelli and J. -M. Pons,Lewis Acids and Selectivity in Organic Synthesis, CRC Press, Inc., Boca Raton, 1996, 334 pp.

    Google Scholar 

  15. Y. Yamamoto and N. Asao,Chem. Rev., 1993,93, 2207.

    Article  CAS  Google Scholar 

  16. I. V. Bodrikov, L. V. Chumakov, A. N. Pryadilova, G. A. Nisnevich, Yu. V. Gatilov, I. Yu. Bagryanskaya V. I. Mamatyuk, G. N. Dolenko, and V. A. BarhashZh. Org. Khim., 1984,20, 2257 [J. Org. Chem. USSR, 1984,20 (Engl. Transl.)].

    CAS  Google Scholar 

  17. V. S. Bogdanov, A. S. Gybin, E. G. Cherepanova, and W. A. Smit,Izv. Akad. Nauk, Ser. Khim., 1981, 2681 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981,30 (Engl. Transl.)].

    Google Scholar 

  18. W. H. Mueller and P. E. Butler,J. Am. Chem. Soc., 1968,90, 2075.

    CAS  Google Scholar 

  19. W. H. Watanabe and L. E. Conlon,J. Am. Chem. Soc., 1957,79, 2828.

    Article  CAS  Google Scholar 

  20. T. Okuyama, T. Fueno, H. Nakatsuji, and J. Furukawa,J. Am. Chem. Soc., 1967,89, 5826.

    Article  CAS  Google Scholar 

  21. P. Cazeau, F. Duboudin, F. Moulines, O. Babot, and J. Dunogues,Tetrahedron, 1987,43, 2075.

    Article  CAS  Google Scholar 

  22. P. Cazeau, F. Duboudin, F. Moulines, O. Babot, and J. Dunogues,Tetrahedron, 1987,43, 2089.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    M. I. Lazareva, Yu. K. Kryschenko, A. D. Dilman & W. A. Smit

  2. Chemistry Department, University of Minnesota-Duluth, 10 University Drive, 55812, Duluth, MN, USA

    A. Hayford & R. Caple

Authors
  1. M. I. Lazareva
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  2. Yu. K. Kryschenko
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  3. A. D. Dilman
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  4. A. Hayford
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  5. R. Caple
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  6. W. A. Smit
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya No. 5, pp. 924–932, May, 1998.

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Lazareva, M.I., Kryschenko, Y.K., Dilman, A.D. et al. Four-component couplingvia a sequence of threeAd E reactions involving arenesulfenyl chloride, two alkyl vinyl ether units, and silicon-containing π-donors as a method for the synthesis of polyfunctional compounds. Russ Chem Bull 47, 895–903 (1998). https://doi.org/10.1007/BF02498158

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  • DOI: https://doi.org/10.1007/BF02498158

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