Aziridination of α, β-unsaturated esters bearing allylic hydroxy groups with 3-acetoxyaminoquinazolinones: evidence for a mechanism comprising Michael addition– …

RS Atkinson, PJ Williams

Index: Atkinson, Robert S.; Williams, Paul J. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 16 p. 1951 - 1959

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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 ...