N-Hetero cyclic carbene catalysis for facile access to Pentasubstituted 4-H Pyran derivatives

Synlett Pub Date : 2024-01-24 DOI:10.1055/a-2253-4365
Xiaolin Peng, Yulin Wang, Yixian Huang, Sheng Zhang, Zhichao Jin, Shi-Chao Ren
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Abstract

The synthesis of multi-substituted 4-H Pyrans derivatives has drawn considerable attention due to its wide application in agrochemicals, pharmaceuticals, and other functional molecules. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed [3+3] annulation reactions between -ketone esters and enynals for quick access to penta-substituted 4-H Pyran derivatives via a regioselective activation of ynals. A series of 4-H Pyrans derivatives bearing various substituents were obtained in moderate to excellent yields. This method may find further applications in the synthesis of structurally diverse 4-H Pyrans derived functional molecules from readily available starting materials.

Abstract Image

利用 N-异环碳烯催化技术轻松获得五代 4-H 吡喃衍生物
多取代 4-H 吡喃衍生物的合成因其在农用化学品、医药和其他功能分子中的广泛应用而备受关注。在此,我们报告了一种 N-杂环碳烯(NHC)催化的  酮酯与烯醛的[3+3]环化反应,通过对炔醛的区域选择性活化,快速获得五取代的 4-H Pyran 衍生物。一系列带有不同取代基的 4-H 吡喃衍生物以中等到极好的收率获得。这种方法可进一步应用于利用现成的起始材料合成结构多样的 4-H 吡喃衍生功能分子。
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