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-Aryl-3-(hydroxymethyl)aziridines

被引：12
|
作者：
Mollet, Karen
D'hooghe, Matthias [1 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Dept Sustainable Organ Chem & Technol, Fac Biosci Engn, B-9000 Ghent, Belgium
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 01期
关键词：
BETA-LACTAMS; BUILDING-BLOCKS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONTAINING LIGANDS; RING EXPANSION; AMINO-ACIDS; AZETIDINES; PROPRANOLOL; DERIVATIVES;
D O I：
10.1021/jo1020932
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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 N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.
引用
收藏
页码：264 / 269
页数：6
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