Department of Chemistry, University of British Columbia, Vancouver, 2036 Main Mall, Vancouver, B.C., V6T 1Z1, Canada.
Chemistry. 2022 Jul 26;28(42):e202201328. doi: 10.1002/chem.202201328. Epub 2022 Jun 9.
The utility of 2-diphenylphosphoryloxy-1,3-dienes for the construction of substituted six-membered nitrogen heterocycles is presented. These dienes undergo boron trifluoride-promoted aza-Diels-Alder reactions when reacted with imines or related species formed in situ using aldehydes and amine derivatives. The stability of the dienes allows this three-component reaction to be carried out with no special precautions to eliminate water or air. Thirty-one examples of this process are presented. The usefulness of the enol phosphate functional group is highlighted in further reactions after the cycloaddition step to generate functionalized piperidenes or pyridines.
本文介绍了 2-二苯膦酰氧基-1,3-二烯在构建取代的六元氮杂环中的应用。这些二烯与亚胺或使用醛和胺衍生物原位形成的相关物种反应时，会发生三氟化硼促进的氮杂 Diels-Alder 反应。二烯的稳定性使得该三组分反应可以在没有特殊措施去除水或空气的情况下进行。本文展示了 31 个该过程的实例。在加成环化步骤之后，烯醇磷酸酯官能团在进一步的反应中具有很高的用途，可以生成官能化的哌啶或吡啶。
