Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides
Maria Bouda, Jeffery A. Bertke, Christian Wolf
Abstract
High Resolution Image Download MS PowerPoint Slide Fluorooxindoles undergo asymmetric Michael addition to para -quinone methides under phase-transfer conditions with 10 mol% of a readily available cinchona alkaloid ammonium catalyst. This reaction affords sterically encumbered, multifunctional fluorinated organic compounds displaying two adjacent chirality centers with high yields, ee ’s and dr ’s.
Topics & Concepts
ChemistryCinchonaConjugateQuinoneCinchona AlkaloidsOrganocatalysisSteric effectsEnantioselective synthesisCatalysisOrganic chemistryAmmoniumMichael reactionChirality (physics)Combinatorial chemistryStereochemistryNambu–Jona-Lasinio modelMathematical analysisQuantum mechanicsQuarkChiral symmetry breakingPhysicsMathematicsSynthesis of Indole DerivativesCarbohydrate Chemistry and SynthesisFluorine in Organic Chemistry