Bronsted acid catalyzed proto-functionalization of enecarbamates and enamides: A convenient route to N,O-acetals
Bronsted acid catalyzed proto-functionalization of enecarbamates and enamides: A convenient route to N,O-acetals
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布朗斯台德酸催化烯氨基甲酸酯和烯酰胺的原官能化：制备 N,O-缩醛的便捷途径
DOI：
10.1016/j.tet.2020.131085
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发表时间：
2020
期刊：
影响因子：
2.1
通讯作者：
Li Yanli
中科院分区：
文献类型：
--
作者：
Ma Xiao-Yan;Zhang Chang-Fei;Hu Xinjun;Zou Wei;Li Yanli
N，O-缩醛是许多具有生物活性的天然产物中的重要结构，这种独特的有机官能团可以作为合成不稳定的N-酰亚胺的有用前体。本文报道了以烯氨基甲酸酯和酰胺为原料，在Bronsted酸条件下，以醇为溶剂和亲核试剂，合成N-氨基甲酰基-N，O-缩醛和N-酰基-N，O-缩醛的简便方法。该方法可用于由一系列烯氨基甲酸酯和酰胺与轻质醇反应制备各种N，O-缩醛，产率较高（52-98%）。(C)2020爱思唯尔有限公司保留所有权利。
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 Bronsted 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%). (C) 2020 Elsevier Ltd. All rights reserved.