Lewis Acid Catalyzed (3+2)‐Cycloaddition of Chiral Pyrimidinyl‐Substituted Cyclopropanes with Nitrosoarenes or Silyl Enol Ethers


Chiral isoxazole and carbocyclic pyrimidine nucleoside analogues have been synthesized by means of (3+2)-cycloadditions of chiral pyrimidinyl-substituted dimethyl cyclopropanedicarboxylates. In the presence of MgI 2 , (3+2)-cycloadditions of chiral pyrimidinyl-substituted cyclopropanes with nitrosoarenes afforded varied chiral isoxazole pyrimidine nucleoside analogues in up to 78% produce and 88-96% ee. Utilizing Nd(OTf) 3 as the catalyst, the annulation response with silyl enol ethers created a series of chiral carbocyclic pyrimidine nucleoside analogues in up to 64% generate, >20:1 dr, and 87-96% ee. The proposed strategies possibly decreased or averted partial racemization.


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