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首页> 外文期刊>Chemistry: A European journal >Organocatalyzed Aldol Reaction between Pyridine-2-carbaldehydes and a-Ketoacids: A Straightforward Route towards Indolizidines and Isotetronic Acids
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Organocatalyzed Aldol Reaction between Pyridine-2-carbaldehydes and a-Ketoacids: A Straightforward Route towards Indolizidines and Isotetronic Acids

机译：吡啶-2-甲醛与α-酮酸之间的有机催化醛醇缩合反应：向吲哚并咪唑和等渗酸的直接途径

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摘要

Enantioselective aldol reactions between substituted pyridine carbaldehydes and a-ketoacids were shown to provide isotetronic acids or their corresponding pyridinium salts, depending on the nature of the substituents on the pyridine ring. The pyridinium salts were generated through nucleophilic attack of the pyridine nitrogen atom onto the reactive keto functional group. Moderate-to-good yields of both compounds were typically obtained and high levels of enantioselectivity were observed by using benzimidazole pyrrolidine I as a catalyst. Hydrogenation of the resulting pyridinium salts led to new indolizidines with high ee values and diastereocontrol. X-ray diffraction studies allowed the determination of the relative configuration of the products. Finally, DFT calculations were performed to rationalize the divergent pathway as a function of the pyridine substituents.
机译：根据吡啶环上取代基的性质，显示出取代的吡啶甲醛与α-酮酸之间的对映选择性醛醇缩合反应可提供等渗酸或它们相应的吡啶鎓盐。吡啶鎓盐是通过吡啶氮原子对反应性酮官能团的亲核攻击而生成的。通常，使用苯并咪唑吡咯烷I作为催化剂，两种化合物的产率均达到中等至良好，并观察到高水平的对映选择性。所得吡啶鎓盐的氢化导致具有高ee值和非对映异构控制的新吲哚并立定。 X射线衍射研究可以确定产品的相对构型。最后，进行DFT计算以合理化发散途径与吡啶取代基的关系。

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