Chen Xiaoye, Au Chi-Ming, Fang Pengyuan, Xue Yunsheng, Leung Ken Cham-Fai, Chan Wai-Lun
The International Joint Institute of Tianjin University-National University of Singapore in Fuzhou, Tianjin University, Tianjin 300072, China.
Department of Chemistry, National University of Singapore, 3 Science Drive, Singapore 117543.
Org Lett. 2025 May 23;27(20):5081-5086. doi: 10.1021/acs.orglett.5c01162. Epub 2025 May 14.
A facile, mild, and scalable late-stage N-alkenylative modification strategy is introduced on 1-indoles, 9-carbazoles, and their structural derivatives and analogues, including alkaloids, bioactive agents, and tryptophan motifs, via chemo- and regioselective phosphine-mediated propiolate hydroamination. Saliently, through this protocol, bisconjugation and macrocyclization on (bis)indolic scaffolds can also be accomplished, with the installation of new α,β-unsaturated ester handles for potential further versatile synthetic manipulations.
通过化学选择性和区域选择性膦介导的丙炔酸酯氢胺化反应，在1-吲哚、9-咔唑及其结构衍生物和类似物（包括生物碱、生物活性剂和色氨酸基序）上引入了一种简便、温和且可扩展的后期N-烯基化修饰策略。值得注意的是，通过该方案，还可以在（双）吲哚支架上实现双共轭和大环化，并安装新的α,β-不饱和酯官能团，用于潜在的进一步多功能合成操作。
