Solvent‐Dependent Enantiodivergent Friedel‐Crafts Reaction of Arylsulfonyl Indoles with 1‐Naphthols

We reported a solvent‐controlled enantiodivergent Friedel‐Crafts reaction of 1‐naphthols with vinylogous imine intermediates, which were generated from arylsulfonyl indoles. This reaction was catalyzed by a single cinchona alkaloid bifunctional organocatalyst and could produce both enantiomers by using toluene or 1,2‐DCE as the solvents. Eyring plot analysis revealed that enthalpy‐entropy compensation dominates this enantiodivergent reaction. DFT calculation was used to probe and compare the R‐ and S‐selective pathways.