A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals.

公开了卡宾催化的不对称烯二醛的化学选择性反应。该反应以优异的选择性提供了一种简洁的双环呋喃并[2,3-b]吡咯衍生物的制备方法。该反应的主要挑战是内二底物中两个醛部分的化学选择性反应。通过实验进行的机理研究表明，我们的化学选择性控制主要是通过不同位点的 Breslow 中间体的还原特性来实现的。还通过高分辨率质谱分析研究了几种副反应过程和相应的副加合物。我们的方法可以有效组装广泛存在于天然产物和药物中的呋喃并[2,3-b]吡咯结构部分及其类似物。