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首页> 外文期刊>Chemistry: A European journal >Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
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Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study

机译：微波辅助的炔丙基乙烯基醚对水杨醛衍生物的有机催化重排：实验和理论研究

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摘要

The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-break ing conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6p electrocyclization, and an aromatization reaction.
机译：描述了微波辅助的咪唑催化的炔丙基乙烯基醚（PVE）到多取代的水杨醛的转化。该反应在仪器上简单，可扩展，并且在起始PVE的炔丙基位置容许不同程度的取代。生成的水杨醛基序包含多种拓扑结构，从简单的芳香族单环到复杂的稠合多环系统。该反应是高度区域选择性的，并且发生在破坏对称的条件下。该反应的制备能力在morintrifolin B的首次全合成中得到了证明。morintrifolinB是从小树Morinda citrifolia L分离出的二苯甲酮代谢物。对该反应进行了DFT研究，计算值与实验结果完全一致。理论上计算出的值支持一种多米诺机制，该机制包括炔丙基克莱森重排，[1,3] -H移位，[1,7] -H移位（烯化），6p电环化和芳构化反应。

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