School of Pharmacy, Xinxiang University, Xinxiang, Henan 453000, P. R. China.
J Org Chem. 2023 May 5;88(9):5982-5996. doi: 10.1021/acs.joc.3c00331. Epub 2023 Apr 20.
A highly selective and divergent synthesis which enabled access to various complex compounds is highly attractive in organic synthesis and medicinal chemistry. Herein, we developed an effective method for divergent synthesis of highly substituted tetrahydroquinolines via Lewis base catalyzed switchable annulations of Morita-Baylis-Hillman carbonates with activated olefins. The reaction displayed switchable [4 + 2] or [3 + 2] annulations via catalyst or substrate control, providing a diverse range of architectures which contained highly substituted tetrahydroquinolines or cyclopentenes with three contiguous stereocenters bearing a quaternary carbon center in high yields with excellent diastereoselectivities and regioselectivities. Furthermore, synthetic utility of this strategy was further highlighted by gram-scale experiments and simple transformations of the products.
在有机合成和药物化学中，高度选择性和多样化的合成方法可以很容易地将医学专业学术文献从英文翻译为简体中文。在这里，我们开发了一种通过路易斯碱催化的 Morita-Baylis-Hillman 碳酸酯与活化烯烃的可切换环加成反应来实现高取代四氢喹啉的发散合成的有效方法。该反应通过催化剂或底物控制显示出可切换的[4+2]或[3+2]环加成反应，提供了多种包含高取代四氢喹啉或环戊烯的结构，其中含有三个连续的立体中心，带有一个季碳原子，产率高，非对映选择性和区域选择性好。此外，通过克级实验和产物的简单转化进一步突出了该策略的合成实用性。
