Disulfide exchange in hydrogen-bonded cyclic assemblies: stereochemical self-selection by double dynamic chemistry

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Samenvatting

Stereoselective cyclization of cystine-based bifunctional 2-ureido-4[1H]-pyrimidinone derivatives in CDCl3 solutions was demonstrated by 1H NMR spectroscopy. Thiolate-catalyzed disulfide exchange in solution led to the equilibration of different diastereomers of 1. At low concentrations, where formation of cyclic assemblies is the dominant mode of association, the molecules act as their own template. At these concentrations the meso diastereomer is formed preferentially, indicating a higher stability of its cyclic assemblies under the applied conditions, in comparison to the other diastereomers.
Originele taal-2Engels
Pagina's (van-tot)5799-5803
Aantal pagina's5
TijdschriftJournal of Organic Chemistry
Volume70
Nummer van het tijdschrift15
DOI's
StatusGepubliceerd - 2005

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