Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening

被引：27

作者：

D'hooghe, Matthias ^{[1
]}

Mollet, Karen ^{[1
]}

Dekeukeleire, Stijn ^{[1
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 03期

关键词：

LITHIUM ALUMINUM-HYDRIDE; HALOGENATED IMINO COMPOUNDS; NUCLEAR-MAGNETIC-RESONANCE; BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE ADDITION; STEREOSPECIFIC SYNTHESIS; AZIRIDINO ALCOHOLS; BUILDING-BLOCKS; ALPHA;

D O I：

10.1039/b919864d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH4 in Et2O. Furthermore, trans- 2-aryl-3-(hydroxymethyl) aziridines were transformed into 2-amino-3-arylpropan-1-ols and anti-2-amino-3-aryl-3-methoxypropan-1-ols by means of an unprecedented ring opening by LiAlH4 and by MeOH, respectively. cis-2-Aryl-3(hydroxymethyl)aziridines were shown to be highly reluctant to undergo ring opening by LiAlH4 and MeOH under similar reaction conditions.

引用

页码：607 / 615

页数：9

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