Organocatalyzed asymmetric Friedel–Craft reactions have enabled the rapid construction of chiral molecules with highly enantioselectivity enriching the toolbox of chemists for producing complex substances. Here, we report N-heterocyclic carbene-catalyzed asymmetric indole Friedel–Crafts alkylation-annulation with α,β-unsaturated acyl azolium as the key intermediate, affording a large variety of indole-fused polycyclic alkaloids with excellent diastereo- and enantioselectivities. The reaction mechanism is also investigated, and the reaction products can be easily converted to highly functionalized indole frameworks with different core structures.

有机催化的不对称Friedel-Craft反应使具有高对映选择性的手性分子得以快速构建，从而丰富了化学家生产复杂物质的工具箱。在这里，我们报道以α，β-不饱和酰基偶氮为主要中间体的N-杂环卡宾催化的不对称吲哚Friedel-Crafts烷基化环化反应，提供了多种具有出色的非对映和对映选择性的吲哚稠合多环生物碱。还研究了反应机理，并且反应产物可以容易地转化为具有不同核心结构的高度官能化的吲哚骨架。