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Brønsted acid catalyzed proto-functionalization of enecarbamates and enamides: A convenient route to N,O-acetals
Tetrahedron ( IF 2.1 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.tet.2020.131085
Ma Xiao-Yan , Zhang Chang-Fei , Hu Xinjun , Zou Wei , Li Yanli

N,O-acetals are important structures found in many bioactive natural products, and this unique organic functional group can serve as a useful synthetic precursor to the unstable N-acylimines. In this paper, a convenient route to synthesize N-carbamoyl-N,O-acetals and N-acyl-N,O-acetals from enecarbamates and enamides in the presence of alcohols as the solvents and nucleophile sources under Brønsted acid conditions was reported. This strategy could be used to prepare various N,O-acetals from a range of enecarbamates and enamides with light alcohols, and the products are obtained in good yields (52–98%).



中文翻译:

布朗斯台德酸催化烯氨基甲酸酯和酰胺的原型官能化:制备N,O-缩醛的便捷途径

N,O-乙缩醛是在许多具有生物活性的天然产物中发现的重要结构,并且这种独特的有机官能团可以用作不稳定的N-酰基酰亚胺的有用合成前体。在本文中,一个方便的途径来合成Ñ氨基甲酰基N,O -acetals和Ñ -acyl- N,O报道从醇作为布朗斯台德酸的条件下的溶剂和亲核试剂的来源的存在enecarbamates和烯酰胺-acetals。该策略可用于由一系列的氨基甲酸酯和酰胺与轻质醇制备各种N,O-乙缩醛,且收率高(52-98%)。

更新日期:2020-03-20
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