Organocatalytic Enantioselective Cross‐Vinylogous Rauhut–Currier Reaction of Methyl Coumalate with Enals |
| |
Authors: | Qiwen Liu Prof?Dr Liansuo Zu |
| |
Institution: | 1. School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing, China;2. Collaborative Innovation Center for Biotherapy, West China Medical School, Sichuan University, Chengdu, China |
| |
Abstract: | The organocatalytic enantioselective intermolecular cross‐vinylogous Rauhut–Currier (RC) reaction of methyl coumalate with α,β‐unsaturated aldehydes is reported, and the enals are activated by iminium catalysis to serve as the Michael acceptors and methyl coumalate is used as an activated diene to generate a latent enolate. The excellent selectivity is driven by the aromaticity of methyl coumalate, and the post transformation of this heterocyclic structure into other electron‐deficient arenes and heterocycles have addressed, in part, the challenging selectivity issues of the intermolecular cross‐RC reactions and the limited scope of iminium catalysis. |
| |
Keywords: | asymmetric catalysis heterocycles organocatalysis reaction mechanisms synthetic methods |
|
|