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Stereoselective cyclization of alkyl N-phthaloyl-4-bromoglutamates to cyclopropane derivatives

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Abstract

The kinetics of the reactions of alkyl N-phthaloyl-4-bromoglutamates with Et3N and KOH was investigated. The reactions proceed stereospecifically to form alkyl 1-phthalimidocyclopropane-r-1,t-2-dicarboxylates. In alcohols, the reactions are accompanied by transesterification. The concerted mechanism accounting for the stereospecificity of these reactions is proposed.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation

    V. P. Krasnov, M. A. Koroleva, T. V. Matveeva, E. A. Zhdanova & A. N. Grishakov

  2. A. N. Severtsov Institute of Ecology and Evolution, Russian Academy of Sciences, 33 Leninsky prosp., 117071, Moscow, Russian Federation

    N. A. Klyuev

Authors
  1. V. P. Krasnov
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  2. M. A. Koroleva
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  3. T. V. Matveeva
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  4. E. A. Zhdanova
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  5. A. N. Grishakov
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  6. N. A. Klyuev
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Krasnov, V.P., Koroleva, M.A., Matveeva, T.V. et al. Stereoselective cyclization of alkyl N-phthaloyl-4-bromoglutamates to cyclopropane derivatives. Russian Chemical Bulletin 50, 644–648 (2001). https://doi.org/10.1023/A:1011356727378

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