Direct Imine Acylation: A Versatile Method for the Synthesis of Nitrogen-Containing Heterocycles, Spirocycles and Natural Products
Direct Imine Acylation: A Versatile Method for the Synthesis of Nitrogen-Containing Heterocycles, Spirocycles and Natural Products
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DOI：
10.1055/s-0035-1562095
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发表时间：
2016-05
期刊：
影响因子：
2
通讯作者：
W. Unsworth;R. Taylor
中科院分区：
文献类型：
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作者：
W. Unsworth;R. Taylor
使用官能化羧酸对亚胺进行 N-酰化（直接亚胺酰化，DIA）可以合成多种含氮杂环化合物。使用偶联剂丙基膦酸酐 (T3P) 对羧酸进行原位活化，然后与亚胺偶联伴侣反应，原位生成 N-酰亚胺离子，然后该离子可以被羧酸中内置的氧、氮、硫或碳基亲核试剂捕获。这种多功能、收敛的方法已用于生成多种产品，包括芳香族和脂肪族杂环、β-内酰胺、氮杂螺环和天然产物。 1 简介 2 DIA 在乌芬酰胺全合成中的应用 3 DIA 与苯甲酸衍生物的应用 4 DIA 与脂肪族羧酸的应用 5 DIA 在 β-内酰胺合成中的应用 6 DIA 在氮杂螺环合成中的应用 7 机理研究 8 结论
Diverse nitrogen-containing heterocyclic compounds can be synthesised by the N-acylation of imines using functionalised carboxylic acids (Direct Imine Acylation, DIA). The carboxylic acids are activated in situ using the coupling agent propylphosphonic acid anhydride (T3P), before reacting with the imine coupling partner to generate N-acyliminium ions in situ, that can then be trapped by oxygen-, nitrogen-, sulfur- or carbon-based nucleophiles built into the carboxylic acid. This versatile, convergent method has been used to generate a wide range of products, including aromatic and aliphatic heterocycles, β-lactams, azaspirocycles and natural products. 1 Introduction 2 DIA in the Total Synthesis of ‘Upenamide 3 DIA with Benzoic Acid Derivatives 4 DIA with Aliphatic Carboxylic Acids 5 DIA in the Synthesis of β-Lactams 6 DIA in the Synthesis of Azaspirocycles 7 Mechanistic Studies 8 Conclusion