Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl α-Amino Acid Derivatives
Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl α-Amino Acid Derivatives
复制标题
用于合成功能化烯丙基 α-氨基酸衍生物的不可逆 Oxy-2-azonia-Cope 重排
DOI：
10.1002/ejoc.201301818
复制
发表时间：
2014-04-01
影响因子：
2.8
通讯作者：
Goeke, Andreas
中科院分区：
文献类型：
--
作者：
Mu, Wenbo;Zhou, Lijun;Goeke, Andreas
报道了一种通过不可逆的氧-2-氮鎓-Cope重排反应合成功能化烯丙基氨基酸衍生物的一般方法。在AlCl_3存在下，甘氨酸亚氨基乙酯与各种β-不饱和酮反应，得到相应的烯丙基氨基酸衍生物。这种方法成功的关键是酰胺键的形成，这使得重排不可逆。该反应体系为合成具有重要应用价值的合成中间体烯丙基甘氨酸衍生物提供了一种新的策略。还进行了该反应的有效且操作简单的三组分版本。
A general method to synthesize functionalized allyl -amino acid derivatives through an irreversible oxy-2-azonia-Cope rearrangement is reported. In the presence of AlCl3, the reaction of imino ethyl glyoxalates with various ,-unsaturated ketones furnished the corresponding allyl -amino acid derivatives. The key to the success of this method is the amide bond formation, which makes the rearrangement irreversible. This reaction system constitutes a new strategy for the synthesis of unusual allyl glycine derivatives, which are valuable synthetic intermediates. An efficient and operationally simple three-component version of this reaction was also performed.