Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 25, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200604
Keywords
Aminocyclopropanes; (3+2)-Cycloadditions; Lewis acids; Nucleosides; Synthetic methods
Categories
Funding
- NSFC [22071046]
- Natural Science Foundation of Henan Province [222300420474]
- Key Project for Science and Technology Research of Henan Provincial Department [21A150001]
- Program for Innovative Research Team in Science and Technology in University of Henan Province [22IRTSTHN003]
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
- [212101510004]
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Chiral isoxazole and carbocyclic pyrimidine nucleoside analogues were synthesized via cycloadditions, with high yields and enantiomeric excess, while avoiding racemization.
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.
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