Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration

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.