Aziridination of alkenes using 3-acetoxyaminoquinazolin-4(3H)ones: nucleophilic attack by the acetoxyamino group on ester-substituted allylic alcohols

Abstract

Allylic alcohols 5 and 7 and their acetates 6 and 8 are aziridinated using 3-acetoxyaminoquinazolinone 1; the preferred sense of diastereoselection in aziridination of 5 is inverted in aziridination of its acetate 6 whereas the preferred sense of diastereoselection from 7 is retained in aziridination of its acetate 8; this is interpreted as evidence for nucleophilic attack by the acetoxyamino nitrogen of 1 on the alkene with hydrogen bonding between the hydroxyl and N-acetoxy group present in aziridination of 5 but absent in the case of 7.