Iliyasov, Taigib M.; Karpenko, Kirill A.; Akulinin, Alexander S.; Fakhrutdinov, Artem N.; Korolev, Viktor A.; Elinson, Michail N.; Vereshchagin, Anatoly N. published the artcile< Stereoselective one-pot five-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines with two and three stereocenters>, Name: Ethyl 3-oxo-3-phenylpropanoate, the main research area is polysubstituted tetrahydropyridine preparation stereoselective; aldehyde ester oxocarboxylic acid one pot five component reaction.
A novel five-component stereoselective synthesis of polysubstituted tetrahydropyridines is reported. The Knoevenagel condensation – Michael addition – Mannich reaction – cyclization – dehydration cascade of aldehydes, esters of 3-oxocarboxylic acids C-H acids and ammonium acetate provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine-3-carboxylates with two stereocenters and 3,5-dialkyl (4RS,5SR,6RS)-5-cyano-2,4,6-triaryl-1,4,5,6-tetrahydropyridine-5,3-carboxylates with three stereocenters in 57-84% yields. It was established that formation of products proceeds via substituted 2-hydroxypiperidines with four stereocenters. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Five bonds are formed as a result of multicomponent process. The formation of single diastereomers was confirmed by singe crystal X-ray diffraction studies and 2D-NMR spectroscopy.
ARKIVOC (Gainesville, FL, United States) published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Name: Ethyl 3-oxo-3-phenylpropanoate.
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