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

页码：264 / 269

页数：6

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