Regioselective and Enantioselective Synthesis of β‐Indolyl Cyclopentenamides by Chiral Anion Catalysis |
| |
Authors: | Dr. Subramani Rajkumar Jiawen Wang Sujuan Zheng Donglei Wang Xueqian Ye Xuejiao Li Prof. Dr. Qian Peng Prof. Dr. Xiaoyu Yang |
| |
Affiliation: | 1. School of Physical Science and Technology ShanghaiTech University, Shanghai, China;2. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China |
| |
Abstract: | The regioselective and enantioselective synthesis of β‐indolyl cyclopentenamides, a versatile chiral building block, by asymmetric addition of indoles to α,β‐unsaturated iminium intermediates has been achieved through chiral anion catalysis. Key to the success of this methodology is the generation of a chiral anion‐paired ketone‐type α,β‐unsaturated iminium intermediate from α‐hydroxy enamides. Preliminary mechanistic studies and DFT calculations are consistent with a mechanism involving multiple, concurrent pathways for isomerization of the initially formed azaallylcation into the key α,β‐unsaturated iminium intermediate, all mediated by the phosphoric acid catalyst. |
| |
Keywords: | chiral anion catalysis organocatalysis indoles reaction mechanisms synthetic methods |
|
|