Synthesis of nitrogen-substituted methylenecyclopropanes by strain-driven Overman rearrangement of cyclopropenylmethyl trichloroacetimidates.

作者: James K. Howard , Chintan Amin , Brendan Lainhart , Jason A. Smith , Jack Rimington

DOI: 10.1021/JO501423U

关键词: StereochemistryHydrolysisMedicinal chemistryNitrogenCatalysisStrain (chemistry)Overman rearrangementChemistry

摘要: Nitrogen-substituted methylenecyclopropanes have been prepared by a strain-driven Overman rearrangement of cyclopropenylmethyl trichloroacetimidates. The reaction proceeds at room temperature and without the need transition-metal catalyst. Furthermore, it has shown that C-3-substituted trichloroacetimidates undergo hydrolytic ring-opening to form allenylcarbinols.

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