Carbonyl group-assisted 1,3-amine addition to α,β-unsaturated aldehydes

Zhenguo Zhang, Mi Ren, Ming-Zhu Lu, Zhenhua Jia, Teck-Peng Loh
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Abstract

An unusual 1,3-addition products were obtained when amines were reacted with α,β-unsaturated aldehydes compounds in the presence of iodine and an oxidant. The versatile unsaturated α-amino acetals are highly useful amino acid derivatives and can be converted to a wide variety of synthetically useful building blocks. Various control experiments have shown that the reaction proceeded via a mechanism involving the formation of imine/enamine intermediates followed by a 1,2-amine group migration reaction.
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羰基辅助 1,3-胺与α、β-不饱和醛的加成反应
当胺与α,β-不饱和醛化合物在碘和氧化剂存在下反应时,得到了一种不寻常的 1,3 加成产物。用途广泛的不饱和 α-氨基乙缩醛是非常有用的氨基酸衍生物,可转化为多种有用的合成构筑物。各种对照实验表明,该反应的机理是先形成亚胺/烯胺中间体,然后发生 1,2-胺基团迁移反应。
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