A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids

被引：0
|
作者：
Valérie Declerck
David J. Aitken
机构：
[1] ICMMO (UMR 8182-CNRS),Laboratoire de Synthèse Organique et Méthodologie
[2] Université Paris-Sud 11,undefined
来源：
Amino Acids | 2011年 / 41卷
关键词：
2-Aminocyclobutanecarboxylic acids; Photochemical [2 + 2] cycloaddition; Chiral resolution; Epimerization; Oxazolidin-2-one;
D O I：
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中图分类号：
学科分类号：
摘要：
The synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids has been refined to improve both the efficiency and the simplicity. These improvements provide a shorter and easier access to the racemic cis-cyclobutane β-amino acid core. Derivatization of this material with a chiral non-racemic oxazolidin-2-one allows easy diastereoisomeric separation and presents the advantage of allowing the non-destructive cleavage of the chiral auxiliary either by hydrolysis or by ammonolysis, thus providing an efficacious access to N-protected derivatives of all four stereoisomers of Boc-2-aminocyclobutanecarboxylic acid.
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页码：587 / 595
页数：8
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