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Asymmetric C-C Bond Forming Reactions by Chiral Crown Catalysts; Darzens Condensation and Nitroalkane Addition to the Double Bond
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1997
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Asymmetric CatalysisSugar DerivativeChemical EngineeringCross-coupling ReactionEngineeringNovel OrganocatalystsDarzens CondensationOrganic ChemistryDouble BondEfficient CrownCatalysisChiral Crown CatalystsChemistryLiquid-liquid PhaseOrganometallic CatalysisDeep Eutectic SolventSynthetic ChemistryEnantioselective Synthesis
A new, efficient crown ether 1 anellated to a sugar derivative has been prepared which shows significant asymmetric induction as phase transfer catalyst in the Michael addition of 2-nitropropane to chalcone (60% ee for the S antipode) and in the Darzens condensation of phenacyl chloride and benzaldehyde (64% ee), simultaneously changing the PT process from solid-liquid to liquid-liquid phase.