Diastereoselective control through hydrogen bonding in the aziridination of the chiral allylic alcohols by acetoxyaminoquinazolinone.

作者: Murat Cakici , Semistan Karabuga , Hamdullah Kilic , Sabri Ulukanli , Ertan Şahin

DOI: 10.1021/JO902092S

关键词: Allylic rearrangementChemistryQuinazolinoneSelectivityCarbonyl groupKetoneAllylic alcoholAlcoholOrganic chemistryHydrogen bond

摘要: A high diastereoselectivity (up to >99:1) is found for the aziridinations of chiral allylic alcohols with acetoxyaminoquinazolinone (Q-NHOAc). The selectivity explained in terms hydrogen bonding between hydroxy functionality alcohol and remote carbonyl group quinazolinone.

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