Palladium(0)-catalyzed syntheses of cyclopentenyl-nucleoside analogues

The N-benzoylamino-2-cyclopenten-1-ol, derived from the nitrosocarbonyl hetero Diels-Alder cycloaddition reaction followed by the mild reductive N-O bond cleavage, allows for the preparation of cyclopentenyl-nucleoside analogues through the palladium(0)-catalyzed addition of both purine and pyrimidine heterobases to the allylic acetate derivative with retention of the starting material stereochemistry. A systematic study is performed on different heterobases to test the general application of the protocol.