<i>N</i>-Heterocyclic Carbene-Catalyzed Regio- and Enantioselective C7-Alkylation of 4-Aminoindoles with α-Bromoenals
Chenghao Tang, Hui Cai, Chaoyang Song, Xiang Wang, Zhichao Jin, Tingting Li
Abstract
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.
Topics & Concepts
ChemistryIndole testEnantioselective synthesisAlkylationCarbeneCatalysisCombinatorial chemistryStereochemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsCatalytic Cross-Coupling Reactions