Regio‐ and Enantioselective [3+2] Cycloaddition of α‐Purine Substituted Acrylates with Allenes: An Approach to Chiral Carbocyclic Nucleosides

N‐Heteroaromatic substituted acrylates are employed in the phosphine‐catalyzed [3+2] annulation with allenes for the first time, affording regiospecific carbocyclic nucleoside analogues in an α‐addition manner. Various chiral carbocyclic nucleoside analogues containing a quaternary stereocenter and...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-08, Vol.360 (15), p.2813-2819
Main Authors: Gao, Yao‐Wei, Niu, Hong‐Ying, Zhang, Qi‐Ying, Xie, Ming‐Sheng, Qu, Gui‐Rong, Guo, Hai‐Ming
Format: Article
Language:English
Subjects:
[3+2] cycloaddition
AC generators
Acrylates
Antiretroviral drugs
carbocyclic nucleosides
Chemical reactions
Cycloaddition
Enantiomers
enantioselective
N-heteroaromatic substituted acrylates
Nucleosides
Organic chemistry
Protease inhibitors
regioselective
Substitutes
Substrates
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Summary:N‐Heteroaromatic substituted acrylates are employed in the phosphine‐catalyzed [3+2] annulation with allenes for the first time, affording regiospecific carbocyclic nucleoside analogues in an α‐addition manner. Various chiral carbocyclic nucleoside analogues containing a quaternary stereocenter and a C=C double bond are generated in good yields (up to 90% yield) and excellent enantioselectivities (up to 97% ee). α‐Purine‐containing disubstituted acrylate and α‐benzimidazole substituted acrylate are also suitable substrates for this reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800523