Stereoselective cyclization of alkyl N-phthaloyl-4-bromoglutamates to cyclopropane derivatives |
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| Authors: | Krasnov V P Koroleva M A Matveeva T V Zhdanova E A Grishakov A N Klyuev N A |
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| Institution: | (1) Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation;(2) A. N. Severtsov Institute of Ecology and Evolution, Russian Academy of Sciences, 33 Leninsky prosp., 117071 Moscow, Russian Federation |
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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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| Keywords: | glutamic acid cyclopropane-1 2-dicarboxylic acid transesterification cyclization |
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