Diastereoselective control through hydrogen bonding in the aziridination of the chiral allylic alcohols by acetoxyaminoquinazolinone

J Org Chem. 2009 Dec 18;74(24):9452-9. doi: 10.1021/jo902092s.


A high diastereoselectivity (up to >99:1) is found for the aziridinations of chiral allylic alcohols with acetoxyaminoquinazolinone (Q-NHOAc). The selectivity is explained in terms of hydrogen bonding between the hydroxy functionality of the allylic alcohol and the remote carbonyl group of the quinazolinone.