By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as the electron-withdrawing group) as a substrate, we discovered a (DHQ)₂AQN-catalyzed method for high diastereo- and enantioselectivity of those products. The reaction path has been determined by isolating the reaction intermediates, and density functional theory calculations support these findings. Beyond providing a synthetic approach, this work illustrated the compounds’ possible use in antitumor activity.

中文翻译：

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不对称双迈克尔受体的Domino Michael/Oxa-Michael反应获得双环呋喃[2,3-b]吡咯

通过创建不对称双迈克尔受体1，我们能够使用多米诺迈克尔/氧杂迈克尔反应合成非芳香族稠合双环呋喃[2,3- b ]吡咯核。采用苯甲酰乙腈2d（CN作为吸电子基团）作为底物，我们发现了一种(DHQ) ₂ AQN催化的方法，该方法具有高非对映和对映选择性。通过分离反应中间体确定了反应路径，密度泛函理论计算支持了这些发现。除了提供合成方法之外，这项工作还说明了这些化合物在抗肿瘤活性中的可能用途。