mannich-bases has been researched along with ethyl-acetoacetate* in 2 studies
2 other study(ies) available for mannich-bases and ethyl-acetoacetate
| Article | Year |
|---|---|
Mechanistic details of amino acid catalyzed two-component Mannich reaction: experimental study backed by density functional calculations.
The role of pH-dependent ionic structures of L-amino acids in catalysis has been investigated for the two-component Mannich reactions between dimethyl malonate (DMM)/ethyl acetoacetate (EAA) and imines. As catalysts, L-amino acids performed well, even better than corresponding base catalysts and provided the β-amino carbonyl compounds in very high yields. Density functional calculations were used to gain the mechanistic insight of the reaction. High catalytic efficiency of amino acids was attributed to the facile formation of carbanion intermediate through barrierless transition state TS1 (- 19.43 kcal/mol) and then its stabilization owing to carbanion interaction with protonated amino acid. Topics: Acetoacetates; Amino Acids; Catalysis; Glutamic Acid; Hydrogen-Ion Concentration; Imines; Malonates; Mannich Bases; Molecular Structure; Stereoisomerism | 2019 |
Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding α-methylamino acid products.
Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L(4)Co(O(2)CCH=NCH(3))](2+) [L(4) = (en)(2) (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)NO(2)]NHCH(3))]ZnCl(4) and rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)COCH(3)]NHCH(3))]ZnCl(4), were established by X-ray diffraction. Topics: Acetoacetates; Cobalt; Coordination Complexes; Crystallography, X-Ray; Malonates; Mannich Bases; Methane; Molecular Conformation; Nitroparaffins; Stereoisomerism; Water | 2013 |