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) …

K Mollet, M D'hooghe, N De Kimpe

文献索引：Mollet, Karen; D'Hooghe, Matthias; De Kimpe, Norbert Journal of Organic Chemistry, 2011 , vol. 76, # 1 p. 264 - 269

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被引用次数: 10

摘要

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 ...