Aziridination of alkenes using 3-acetoxyaminoquinazolin-4(3H)ones: nucleophilic attack by the acetoxyamino group on ester-substituted allylic alcohols
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 18,p. 2031-2032
- https://doi.org/10.1039/c39940002031
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.Keywords
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