Serendipitous One-Step Synthesis of Cyclopentene Derivatives from 5′-Deoxy-5′-Heteroarylsulfonylnucleosides as Nucleoside-Derived Julia–Kocienski Reagents

02 August 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A serendipitous one-step transformation of 5′-deoxy-5′-heteroarylsulfonylnucleosides into cyclopentene derivatives is reported. This unique transformation likely proceeds via a domino reaction initiated by α-deprotonation of the heteroaryl sulfone and subsequent elimination reaction to generate a nucleobase and an α,β-unsaturated sulfone that contains a formyl group. The Michael addition of the nucleobase to the α,β-unsaturated sulfone and subsequent intramolecular Julia–Kocienski reaction eventually generate the cyclopentene ring. Heteroarylthio and acylthio groups can be incorporated into the cyclopentene core in place of the nucleobase by conducting this reaction in the presence of a heteroarylthiol and a thiocarboxylic acid, respectively. Cis,cis-trisubstituted cyclopentene derivatives are obtained as a single stereoisomer from ribonucleoside-derived Julia–Kocienski sulfones.


Domino reaction
Julia-Kocienski reaction
Carbocyclic nucleoside

Supplementary materials

Supporting Information
Experimental procedures, characterization data, and NMR spectra for new compounds. X-ray crystal data for 5.


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