Muriel Bastian, Gagnebin Alec, Waser Jerome
Laboratory of Catalysis and Organic Synthesis , Institut des Sciences et Ingénierie Chimique , Ecole Polytechnique Fédérale de Lausanne , Lausanne , Ch-1015 , Switzerland . Email:
Chem Sci. 2019 Oct 8;10(46):10716-10722. doi: 10.1039/c9sc03790j. eCollection 2019 Dec 14.
We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yields were obtained for a broad range of cyclopropene and cyclopropylaniline derivatives. The reaction was highly diastereoselective when using difluorocyclopropenes together with a removable substituent on the cyclopropylaniline, giving access to important building blocks for medicinal chemistry. With efficient methods existing for the synthesis of both reaction partners, our method grants a fast access to highly valuable bicyclic scaffolds with three contiguous stereocenters.
我们报道了具有全碳季中心的双环[3.1.0]己烷的汇聚合成，即环丙烯与环丙基苯胺的(3 + 2)环化反应。使用有机或铱光氧化还原催化剂以及蓝色发光二极管照射，对于多种环丙烯和环丙基苯胺衍生物都能获得良好的产率。当使用二氟环丙烯与环丙基苯胺上的可去除取代基时，该反应具有高度的非对映选择性，从而获得了药物化学的重要构建块。由于现有的两种反应底物都有高效的合成方法，我们的方法能够快速获得具有三个相邻立体中心的高价值双环骨架。
