Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.
Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5438-5442. doi: 10.1002/anie.201901025. Epub 2019 Mar 12.
The basic industrial feedstock isoprene was employed as a building block to install prenyl and reverse-prenyl groups onto indoles. The regioselectivity can be manipulated by the choice of metal hydride. Reverse-prenylated indoles were attained with high selectivity when using Rh-H. By switching to a Pd-H catalyst, selectivity toward prenylated indoles was achieved. This regiodivergent method also features high atom economy without stoichiometric byproduct formation.
基本的工业原料异戊二烯被用作构建块，将prenyl 和 reverse-prenyl 基团安装到吲哚上。通过选择金属氢化物，可以控制区域选择性。使用 Rh-H 时，可以高选择性地得到 reverse-prenylated 吲哚。通过切换到 Pd-H 催化剂，可以实现prenylated 吲哚的选择性。这种区域发散的方法还具有高原子经济性，没有化学计量的副产物形成。
