Desymmetrization of Meso-Diamine with Enantiopure 3-N,N-Diacylaminoquinazolin-4(3H)-Ones

The title compounds (DAQs) are chiral when the two N-acylgroups are different because of the absence of rotation around theN–N bond (a chiral axis). Enantiopure DAQs have been obtained byincorporation of a chiral centre in enantiopure form bearing a chiralsubstituent in the 2-position of the quinazolinone, followed by separationof diastereoisomers. One of these diastereoisomers reacts withmeso-diamine to give N-(2-aminocyclohexyl)benzamide ( 95%ee).