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

被引:34
作者
ten Cate, AT [1 ]
Dankers, PYW [1 ]
Sijbesma, RP [1 ]
Meijer, EW [1 ]
机构
[1] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
关键词
D O I
10.1021/jo0501238
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective cyclization of cystine-based bifunctional 2-ureido-4[1H]-pyrimidinone derivatives in CDCl3 solutions was demonstrated by H-1 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.
引用
收藏
页码:5799 / 5803
页数:5
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