Transformation of trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-Aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-Aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2

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• 作者：Karen Mollet ; Matthias D鈥檋ooghe ; Norbert De Kimpe
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：January 7, 2011
• 年：2011
• 卷：76
• 期：1
• 页码：264-269
• 全文大小：846K
• 年卷期：v.76,no.1(January 7, 2011)
• ISSN：1520-6904

文摘

trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH₄ in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH₄ to afford 3-aryl-2-(ethylamino)propan-1-ols.