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High-pressure accelerated asymmetric organocatalytic friedel-crafts alkylation of indoles with enones: Application to quaternary stereogenic centers construction

An organocatalytic Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated ketones was found to be efficiently accelerated under high-pressure conditions with a low loading of chiral primary amine salts with good yield and enantioselectivity up to 90%. This approach also allows, for the first time, selected indole derivatives containing quaternary stereogenic centers to be obtained from prochiral beta,beta-disubstituted enones with an enantioselectivity up to 80%.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis