Synthesis of optically active cyclopentene derivatives by a novel domino reaction

Domino reactions are useful for the efficient synthesis of complex compounds. We have discovered that the treatment of Julia-Kocienski sulfones derived from nucleosides with bases such as DBU affords cyclopentene nucleosides in one step via a novel domino reaction. In addition, we discovered that the same reaction in the presence of a nucleophile such as a thiol or a thiocarboxylic acid provides cyclopentenes in which the nucleobase is replaced by the nucleophile. The resulting cyclopentenes are expected to be useful as synthetic intermediates for biologically active carbocyclic nucleosides and cyclopentanes.

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