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

Abstract

Abstract 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. magnified image