33407-36-2

Upstream product

• 18925-69-4 N,N-dimethyl-2-phenylacetamide 
• 103-26-4 methyl cinnamate 
• 109292-20-8 potassium N,N-dimethylphenylacetamide enolate 
• 79237-58-4 sodium salt of phenylacetic acid dimethylamide 
• 78175-83-4 lithium N,N-dimethylphenylacetamide enolate 

Relevant academic research and scientific papers

REGIO- AND STEREOSELECTIVITY IN THE ADDITION OF METAL N,N-DIMETHYLPHENYLACETAMIDE ENOLATES TO SOME CONJUGATED CARBONYL COMPOUNDS

The nucleophilic addition of lithium, sodium, potassium and bromomagnesium N,N-dimethylphenylacetamide enolates to cinnamic aldehyde, chalcone and methyl cinnamate is studied.The regioselectivity of the reaction is found to depend on the metal counterion and other reaction conditions.The stereoselectivity under kinetic and thermodynamic conditions does not depend on the metal.The reactivity of the amide-enolates is compared with the reactivity of other enolates already studied.

Michael Reaction. V. Stereochemistry of the NaNH2 Catalyzed Two-Step Reaction Between Phenylacetic Acid Dialkyl Amides and Methyl Cinnamate or Cinnamic Acid Dialkyl Amides

The reaction is investigated between sodium-metallated (NaNH2) phenylacetic acid dialkyl amides and methyl cinnamate or cinnamic acid dialkyl amides.The thermodynamic equilibrium between the diastereomeric 2,3-diphenylglutaric acid amidoesters or diamides is 5/95 in favour of the threo-isomer.Under kinetic conditions the stereochemistry of the reaction depends on the nature of the donor and the solvent. - Keywords: 2,3-Diphenylglutaric acid derivatives; Sodium amide catalyzed reaction; Stereochemistry; Thermodynamic and kinetic control over configuration