Enantioselective Organocatalytic Michael Addition to Unsaturated Indolyl Ketones
Dmitri Trubitsõn, Jevgenija Martõnova, Marina Kudrjašova, Kristin Erkman, Ivar Järving, Tõnis Kanger
Abstract
-alkylated indoles with α-branched alkyl substituents from the corresponding unsaturated indolyl ketones via a Michael addition has been developed. The resulting products were obtained in high enantioselectivities and in good yields. Various nucleophiles (nitroalkanes, malononitrile, malonic esters) can be used. The substitution pattern of the indole ring had no significant impact on the reaction outcome. Both electron-withdrawing and electron-donating substituents in any position of the heteroaromatic ring were well-tolerated.
Topics & Concepts
ChemistryEnantioselective synthesisMichael reactionMalononitrileIndole testRing (chemistry)AlkylNucleophileOrganocatalysisOrganic chemistryAlkylationAddition reactionMedicinal chemistryCatalysisAsymmetric Synthesis and CatalysisSynthesis of Indole DerivativesChemical Synthesis and Reactions