Diastereoselective Formation of Methylene-Bridged Glycoluril Dimers.
The acid-catalyzed formation of methylene-bridged glycoluril dimers yields the C(2)(v)()-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.
Witt
D
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, and Chemical Faculty, Technical University of Gdansk, Narutowicza St. 11/12, 80-952 Gdansk, Poland.
Lagona
J
Damkaci
F
Fettinger
JC
Isaacs
L