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Sulfur ylides. 12. Optically active keto stabilized sulfur ylide obtained from L-proline: synthesis and study

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Abstract

Optically active keto stabilized sulfur ylide was synthesized from L-proline. The reactions of the ylide with methyl acrylate and methyl vinyl ketone afforded 1,2-disubstituted cyclopropanes. In the case of acrylonitrile, a mixture of 1,2- and 1,1-disubstituted cyclopropanes was obtained. Acylation of the ylide with acetic anhydride gave twice stabilized sulfur ylide.

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References

  1. S. N. Lakeev, I. Z. Mullagalin, F. Z. Galin, I. O. Maidanova, G. F. Vafina, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2002, 951 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1035].

    Google Scholar 

  2. V. K. Mavrodiev, I. I. Furlei, S. N. Lakeev, F. Z. Galin, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1999, 2100 [Russ. Chem. Bull., 1999, 48, 2077 (Engl. Transl.)].

    Google Scholar 

  3. F. Z. Galin, S. N. Lakeev, L. F. Chertanova, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1998, 2376 [Russ. Chem. Bull., 1998, 47, 2304 (Engl. Transl.)].

    Google Scholar 

  4. F. Z. Galin, S. N. Lakeev, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1997, 2008 [Russ. Chem. Bull., 1997, 46, 1904 (Engl. Transl.)].

  5. F. Z. Galin, S. N. Lakeev, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1996, 165 [Russ. Chem. Bull., 1996, 45, 156 (Engl. Transl.)].

    Google Scholar 

  6. S. N. Lakeev, F. Z. Galin, L. M. Khalilov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 1992, 720 [Bull. Russ. Acad. Sci., Div. Chem. Sci., 1992, 41, 566 (Engl. Transl.)].

    Google Scholar 

  7. G. A. Tolstikov, F. Z. Galin, S. N. Lakeev, L. M. Khalilov, and V. S. Sultanova, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 612 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 535 (Engl. Transl.)].

    Google Scholar 

  8. L. M. Khalilov, V. S. Sultanova, S. N. Lakeev, F. Z. Galin, L. F. Chertanova, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2298 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 2011 (Engl. Transl.)].

    Google Scholar 

  9. R. Glaser, M. A. Bernstein, and A. Balan, Magn. Res. Chem., 1991, 29, 766.

    Google Scholar 

  10. G. A. Tolstikov, F. Z. Galin, and S. N. Lakeev, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1187 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 1008 (Engl. Transl.)].

    Google Scholar 

  11. M. F. Ancell and S. S. Brown, J. Chem. Soc., 1957, 1788.

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Authors and Affiliations

  1. Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    S. N. Lakeev, I. Z. Mullagalin, F. Z. Galin, I. O. Maidanova & M. F. Abdullin

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  1. S. N. Lakeev
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  2. I. Z. Mullagalin
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  3. F. Z. Galin
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  4. I. O. Maidanova
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  5. M. F. Abdullin
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Lakeev, S.N., Mullagalin, I.Z., Galin, F.Z. et al. Sulfur ylides. 12. Optically active keto stabilized sulfur ylide obtained from L-proline: synthesis and study. Russian Chemical Bulletin 51, 2230–2233 (2002). https://doi.org/10.1023/A:1022131201542

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  • DOI: https://doi.org/10.1023/A:1022131201542

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