33912-78-6

Upstream product

• 33831-72-0 ethyl 3-amino-3-phenylprop-2-enoate 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-24-7 acetic anhydride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 98-86-2 acetophenone 
• 75-36-5 acetyl chloride 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 4114-31-2 ethylhydrazine carboxylate 
• 60-35-5 acetamide 
• 53256-19-2 ethyl (Z)-3-amino-3-phenylacrylate 

Downstream Products

• 76569-84-1 2-methyl-4-phenyl-6H-1,3-oxazin-6-one 
• 876345-32-3 2-chloro-5-(ethoxycarbonyl)-6-phenylnicotinaldehyde 
• 7554-23-6 ethyl 3-acetamido-3-phenylpropanoate 

Relevant academic research and scientific papers

Highly efficient and facile synthesis of β-enaminones catalyzed by diphenylammonium triflate

Abstract: The catalytic performance of diphenylammonium triflates as an organocatalyst in the synthesis of β-enaminones from various substituted β-diketones and amides (or amines) were evaluated. A wide range of β-enaminones were efficiently synthesized in good to excellent yields under mild reaction conditions. Applying diphenylammonium triflate (DPAT) as catalyst makes this protocol cost-effective, low corrosive and easy to handle. Graphic abstract: [Figure not available: see fulltext.].

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Preparation of highly substituted (β-acylamino)acrylates via iron-catalyzed alkoxycarbonylation of N-vinylacetamides with carbazates

An efficient iron(ii)-catalyzed alkoxycarbonylation reaction between N-vinylacetamides and carbazates is reported. The corresponding useful highly substituted (β-acylamino)acrylates could be obtained in reasonable to good yields and stereoselectivity under mild reaction conditions. This journal is

Iridium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

The iridium-catalyzed asymmetric hydrogenation of 13 different β-dehydroamino acid derivatives to give optically active β-amino acid esters has been examined. Readily accessible monodentate octahydrobinaphthol- based phosphoramidites were used as chiral ligands. Good to excellent enantioselectivities and yields were obtained for the E isomers, whereas poorer catalyst performance was found for the Z isomers. Importantly, to obtain high enantioselectivity, substitution at the 3,3′-positions of the ligands was necessary. Enantioselectivities of up to 94% ee were achieved under optimized conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Development of practical rhodium phosphine catalysts for the hydrogenation of β-dehydroamino acid derivatives

The rhodium-catalyzed asymmetric hydrogenation of various β-dehydroamino acid derivatives to give optically active β-amino acids has been examined. Chiral monodentate 4,5-dihydro-3H-dinaphthophosphepines, which are easily tuned and accessible in a multi-10-g scale, have been used as ligands. The enantioselectivity is largely dependent on the nature of the substituent at the phosphorous atom and on the structure of the substrate. Applying optimized conditions up to 94% ee was achieved.

Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed.

C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin

Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C1-symmetric bisphosphine ligands bound to transition metals.

E-ISOMERIC β-AROMATIC OR HETEROAROMATIC SUBSTITUTED β-ACYLAMINO-ACRYLATES AND METHODS OF PREPARING THE SAME

E-isomeric ?-(hetero) aromatically substituted acylaminoacrylates are of great economic interest since with them, by means of hydration, precursors of appropriately substituted (?-amino acids can be prepared and, by doing so, lead to higher enantio-select

Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric β-acylamido acrylates

The highly stereoselective synthesis of a chiral silylphospholane has been described, which can be advantageously used as a building block under base-free conditions for the construction of diphosphines related to DuPHOS. The utility of silylphospholane is shown in the synthesis of a new bisphospholane ligand 1 (MalPHOS), which is characterized by a maleic anhydride backbone. The ligand forms with Rh(I) a complex with a larger bite angle P-Rh-P than the analogue Me-DuPHOS complex. Both complexes have been tested in the asymmetric hydrogenation of unsaturated α- and β-amino acid precursors of pharmaceutical relevance. In several cases, the new catalyst was superior in comparison to the Me-DuPHOS complex, in particular when (Z)-configured β-acylamido acrylates were used as substrates.

Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-β-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-β-(acylamino)acrylates (98-99% ee) and (Z)-β-(acylamino)acrylates (92-95% ee) based on phosphoramidites 2 and 3, respectively. Copyright