Details

Autor(en) / Beteiligte

• Wang, Hai‐Xia
• Zhang, Mi‐Mi
• Xie, Ming‐Sheng
• Guo, Hai‐Ming

Titel

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

Ist Teil von

• European journal of organic chemistry, 2022-07, Vol.2022 (25), p.n/a

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Chiral isoxazole and carbocyclic pyrimidine nucleoside analogues were synthesized via (3+2)‐cycloadditions of chiral pyrimidinyl‐substituted dimethyl cyclopropanedicarboxylates. In the presence of MgI2, (3+2)‐cycloadditions of chiral pyrimidinyl‐substituted cyclopropanes with nitrosoarenes afforded diverse chiral isoxazole pyrimidine nucleoside analogues in up to 78 % yield and 88–96 % ee. Using Nd(OTf)3 as the catalyst, the annulation reaction with silyl enol ethers generated a series of chiral carbocyclic pyrimidine nucleoside analogues in up to 64 % yield, >20 : 1 dr, and 87–96 % ee. The proposed methods either reduced or avoided partial racemization. Chiral isoxazole and carbocyclic pyrimidine nucleoside analogues were synthesized by (3+2)‐cycloadditions of chiral pyrimidinyl‐substituted dimethyl cyclopropanedicarboxylates. With MgI2 or Nd(OTf)3 as the catalysts, diverse chiral pyrimidine nucleoside analogues were obtained in 87–96 % ee. The proposed methods either reduced or avoided partial racemization.