Enantioselective Indole Insertion Reactions of α-Carbonyl Sulfoxonium Ylides
Alexandria N. Leveille, Radell Echemendía, Anita E. Mattson, Antonio C. B. Burtoloso
Abstract
The first example of organocatalytic enantioselective C-H insertion reactions of indoles and sulfoxonium ylides is reported. Under the influence of phosphoric acid catalysis, levels of enantiocontrol in the range of 20-93% ee and moderate yields (up to 50%) were achieved for 29 examples in formal C-H insertion reactions of free indoles and α-carbonyl sulfoxonium ylides. No nitrogen protection on the indole is necessary.
Topics & Concepts
Enantioselective synthesisChemistryIndole testPhosphoric acidInsertion reactionCatalysisOrganocatalysisCombinatorial chemistryOrganic chemistryCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods