Stereospecific Synthesis of Highly Substituted Piperazines via an One-Pot Three Component Ring-Opening Cyclization from <i>N</i>‑Activated Aziridines, Anilines, and Propargyl Carbonates

A simple and efficient one-pot three-component synthetic route to highly substituted and functionalizable piperazines in high yields with excellent stereoselectivity (de, ee >99%) is reported. The SN2-type ring-opening of N-activated aziridines by anilines followed by Pd-catalyzed annulation with propargyl carbonates gives rise to the final piperazine products.本文报道了一条简洁高效的一锅法三组分合成路径，可用于制备高取代度且可功能化的哌嗪（piperazines），产物收率优异且立体选择性极佳（非对映选择性de、对映选择性ee均大于99%）。该合成路线以苯胺类化合物（anilines）对N-活化氮丙啶（aziridines）进行SN2型开环，随后与炔丙基碳酸酯（propargyl carbonates）发生钯催化环化反应，最终得到目标哌嗪产物。