Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, United States.
J Org Chem. 2021 May 21;86(10):7028-7037. doi: 10.1021/acs.joc.1c00032. Epub 2021 May 5.
Oxidopyridinium ions bearing an ester group at the 5-position undergo (4 + 3) cycloaddition reaction to afford congeners of 7-azabicyclo[4.3.1]decane. The reaction generally proceeds in high yield, although an excess of diene is often required to achieve such yields. The reaction is highly regioselective, but not / selective. It appears the cycloaddition process can be either kinetically or thermodynamically controlled, depending on the nature of the diene used and the reaction time. An intramolecular Heck reaction was used to demonstrate that some chemistry is possible with the cycloadducts.
带有 5-位酯基的氧化吡啶鎓离子经历（4 + 3）环加成反应，生成 7-氮杂双环[4.3.1]癸烷的同系物。该反应通常以高产率进行，尽管通常需要过量的双烯才能达到这样的产率。该反应具有高度的区域选择性，但不是选择性的。似乎环加成过程可以是动力学控制或热力学控制的，这取决于所使用的双烯的性质和反应时间。我们使用分子内 Heck 反应证明了一些环加成产物具有一定的化学反应性。
