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Diastereoselective Formation of Methylene-Bridged Glycoluril Dimers

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journal contribution
posted on 16.02.2000, 00:00 by Dariusz Witt, Jason Lagona, Fehmi Damkaci, James C. Fettinger, Lyle Isaacs
The acid-catalyzed formation of methylene-bridged glycoluril dimers yields the C2v-diastereomer selectively. Product resubmission experiments establish that the selectivity is the result of thermodynamic control. A modified synthetic route is presented that allows for the preparation of unsymmetrically substituted dimers. We present the X-ray crystal structures of both diastereomers. This class of compounds is useful for studies of self-assembly in aqueous solution.