N -Heterocyclic Carbene-Catalyzed Regio- and Enantioselective C7-Alkylation of 4-Aminoindoles with α-Bromoenals

作者：Chenghao Tang, Hui Cai, Chaoyang Song, Xiang Wang, Zhichao Jin, Tingting Li · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.3c04266 · 被引用次数：10 · 研究领域：N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Synthetic Organic Chemistry Methods、Catalytic Cross-Coupling Reactions

The first carbene-catalyzed regio- and enantioselective indole C7-alkylation reaction between 4-aminoindoles and α-bromoenals is disclosed. The corresponding indole products could be obtained in moderate to good yields with good to excellent enantioselectivities. The evaluation of antibacterial activity against Psa revealed that nine of the C7-functionalized indoles exhibited superior inhibitory activities compared to the positive controls TC and BT. Our approach provides an efficient strategy to introduce a chiral chain into the C7 position of indole compounds, with potential applications evaluated in pesticide development.