An Unprecedented Ring Transformation of a 4-(Aminomethyl)oxazoline Derivative to a 4-(Hydroxymethyl)imidazoline

被引：2
作者：
Schulz, Marvin [1 ]
Christoffers, Jens [1 ]
机构：
[1] Carl von Ossietzky Univ Oldenburg, Inst Chem, D-26111 Oldenburg, Germany
来源：
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 01期
关键词：
heterocycles; oxazolines; imidazolines; pyridines; chiral ligands; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE HYDROSILYLATION; HENRY REACTIONS; AMINO-ACIDS; COMPLEXES; LIGANDS; KETONES; THIOSTREPTON; OXIDATION; MICHAEL;
D O I：
10.1055/s-0033-1340044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An optically active 4-(azidomethyl)-2-(2-pyridyl)oxazoline was prepared starting from l-serine and picolinic acid. Reduction of the azide moiety gave the corresponding 4-(aminomethyl)-2-(2-pyridyl)oxazoline, which is not a stable compound but readily undergoes ring-transformation rearrangement to furnish a 4-(hydroxymethyl)-2-(2-pyridyl)imidazoline. After Boc protection of the amidine function, the material could be further converted into the 4-(aminomethyl)-2-(2-pyridyl)imidazoline via the respective azidomethyl compound.
引用
收藏
页码：81 / 86
页数：6
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