Aziridination of α,β-unsaturated esters bearing allylic hydroxy groups with 3-acetoxyaminoquinazolinones: evidence for a mechanism comprising Michael addition–SN2 nucleophilic displacement of acetoxy for aziridination of α,β-unsaturated esters
- 1 January 1996
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 16,p. 1951-1959
- https://doi.org/10.1039/p19960001951
Abstract
Aziridinations of the allylic alcohol-bearing α,β-unsaturated esters 6 and 7 and their corresponding acetates 8 and 9 have been carried out under standard conditions using 3-acetoxyaminoquinazolinone 2. Whereas the preferred sense of diastereoselectivity in aziridination of allyl alcohol 6 is inverted by comparison with its acetate 8, the preferred sense of diastereoselectivity is retained in aziridination of allylic alcohol 7 by comparison with its acetate 9. A mechanism is proposed for aziridinations of α,β-unsaturated esters in which Michael addition of the N-acetoxy nitrogen to the β-position of the ester runs ahead of SN2-type nucleophilic displacement of the acetoxy group from nitrogen.Keywords
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