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Stereoselective reactions. II. Asymmetric synthesis of .BETA.-substituted aldehydes by michael reaction using chiral .ALPHA.,.BETA.-unsaturated aldimines.
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1979
Year
Enantioselective SynthesisEngineeringNatural SciencesChiral .Alpha.Diversity-oriented SynthesisAsymmetric SynthesisOrganic ChemistryDiethyl MalonateSynthetic ChemistryStereoselective SynthesisChemistryProposed Stereochemical MechanismAsymmetric CatalysisChiral αStereoselective ReactionsBiomolecular Engineering
The Michael reaction of diethyl malonate with chiral α, β-unsaturated aldimines (4), prepared from crotonaldehyde and optically active α-amino acid tert-butyl esters (3), was found to give the corresponding β-substituted aldehydes (5) in reasonably high optical yields after hydrolysis. A proposed stereochemical mechanism of the reaction is presented.