Organocatalytic Enantioselective Aza‐Michael Addition of Arylamines to 7‐Methide‐7<i>H</i>‐Indoles
Fushuai Li, Zhihong Yang, Yanyan Yang, Qiuhong Huang, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Abstract
Abstract A chiral phosphorus acid catalyzed enantioselective 1,4‐conjugate addition of arylamines to in situ formed 7‐methylene‐7H‐indoles from 7‐indolylmethanols has been developed for the first time. Without additives, the catalytic protocol enabled the formation of 1,4‐adducts with a nitrogen‐containing tertiary carbon stereocenter in 66–96% yield with 70–89% ee under mild conditions. magnified image
Topics & Concepts
Enantioselective synthesisChemistryStereocenterConjugateMichael reactionCatalysisOrganocatalysisAdductMethyleneYield (engineering)Organic chemistryPhosphorusCarbon fibersIndole testMedicinal chemistryMathematical analysisMaterials scienceComposite numberMathematicsMetallurgyComposite materialSynthesis of Indole DerivativesAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality Synthesis