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Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone

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posted on 18.12.2009, 00:00 by Murat Cakici, Semistan Karabuga, Hamdullah Kilic, Sabri Ulukanli, Ertan Şahin, Fatma Sevin
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.