Disulfide exchange in hydrogen-bonded cyclic assemblies: stereochemical self-selection by double dynamic chemistry.
J Org Chem
; 70(15): 5799-803, 2005 Jul 22.
Article
em En
| MEDLINE
| ID: mdl-16018671
ABSTRACT
Stereoselective cyclization of cystine-based bifunctional 2-ureido-4[1H]-pyrimidinone derivatives in CDCl(3) solutions was demonstrated by (1)H 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.
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Bases de dados:
MEDLINE
Assunto principal:
Dissulfetos
/
Hidrogênio
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2005
Tipo de documento:
Article
País de afiliação:
Holanda