Ruhl Julia, Ahles Sebastian, Strauss Marcel A, Leonhardt Christopher M, Wegner Hermann A
Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
Center for Materials Research (LaMa), Justus Liebig University Giessen, Heinrich-Buff-Ring 16, 35392 Giessen, Germany.
Org Lett. 2021 Mar 19;23(6):2089-2093. doi: 10.1021/acs.orglett.1c00249. Epub 2021 Feb 25.
The combination of a Lewis acid-catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction with a photoinduced ring-opening (PIRO) reaction in a domino process has been established as an efficient synthetic method to access medium-sized carbocycles. From readily available electron-rich and electron-poor phthalazines and enamines, respectively, as starting materials, various 9- and 11-membered carbocycles were prepared. This versatile transition-metal-free tool will be valuable for broadening the structural space in biologically active compounds and functional materials.
在多米诺过程中，将路易斯酸催化的逆电子需求狄尔斯-阿尔德（IEDDA）反应与光致开环（PIRO）反应相结合，已被确立为一种合成中等大小碳环的有效方法。分别以易于获得的富电子和贫电子酞嗪及烯胺为起始原料，制备了各种9元和11元碳环。这种通用的无过渡金属工具对于拓宽生物活性化合物和功能材料的结构空间将具有重要价值。
