Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration
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Remir G. Kostyanovsky , Konstantin A. Lyssenko , Gulnara K. Kadorkina , Oleg V. Lebedev , Angelina N. Kravchenko , Ivan I. Chervin and Vasily R. Kostyanovsky
Abstract
The title glycouril 1 was spontaneously resolved into enantiomers by crystallisation from H2O and sorting of conglomerate crystals, then N-chlorination and N-aminomethylation to give 2,3 and 4, respectively, were studied. The absolute configuration 1R,5R-(+) was determined by an X-ray diffraction study of diastereomeric N,N-bis-aminomethyl derivative (–)-4.