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<p>Reactions of 1-aryl-1-chlorocyclopropanes with lithium dialkylamides in THF at 20–50 °C result in corresponding 2-aryl-1-dialkylaminocyclopropames in up to 91% yields. The method uses readily available starting reagents, shows high stereoselectivity, allowing one to obtain isomers with <i>trans</i>-orientation of the incoming dialkylamino group and the aryl fragment as exclusive final products. Similar reactions of 1-(<i>p</i>-tolyl)-1-chlorocyclopanes give not only the corresponding aminocyclopropanes, but also isomeric <i>N</i>,<i>N</i>-dialkyl-(4-cyclopropylbenzyl)amines as products of methyl group deprotonation under the strongly basic conditions used.</p>

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Stereoselective synthesis of 2-aryl-1-dialkylaminocyclopropanes by the reaction of gem-arylchlorocyclopropanes with lithium dialkylamides

  • 期刊论文

  • 发表日期：

    2026年3月1日

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  • V. D. Gvozdev,
  • M. P. Egorov

摘要

Reactions of 1-aryl-1-chlorocyclopropanes with lithium dialkylamides in THF at 20–50 °C result in corresponding 2-aryl-1-dialkylaminocyclopropames in up to 91% yields. The method uses readily available starting reagents, shows high stereoselectivity, allowing one to obtain isomers with trans-orientation of the incoming dialkylamino group and the aryl fragment as exclusive final products. Similar reactions of 1-(p-tolyl)-1-chlorocyclopanes give not only the corresponding aminocyclopropanes, but also isomeric N,N-dialkyl-(4-cyclopropylbenzyl)amines as products of methyl group deprotonation under the strongly basic conditions used.