The N–N bond as a chiral axis: 3-(diacylamino)quinazolin-4(3H)ones as chiral acylating agents
Abstract
Two diasteroisomers of 3-(diacylamino)quinazolinone 5 are separated and identified by crystal structure determinations which confirm the presence of an N–N chiral axis: one diastereoisomer of enantiopure 8 reacts with racemic 1-phenylethylamine exclusively at the 2-acetoxypropanoyl imide carbonyl group and with kinetic resolution to give a 3.6 : 1 ratio of diastereoisomers of 10.