Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst
Hiromichi Egami, Ryo Hotta, Minami Otsubo, Taiki Rouno, Tomoki Niwa, Kenji Yamashita, Yoshitaka Hamashima
Abstract
Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.
Topics & Concepts
Indole testChemistryCatalysisEnantioselective synthesisCombinatorial chemistryRing (chemistry)Phase (matter)Reaction conditionsOrganic chemistryFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCarbohydrate Chemistry and Synthesis