67654-55-1

Upstream product

• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 108-24-7 acetic anhydride 
• 70272-01-4 methyl 3-amino-3-phenylacrylate 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 591-50-4 iodobenzene 
• 106014-57-7 (E)-methyl 3-acetamidoacrylate 
• 86971-60-0 (Z)-3-amino-3-phenylacrylic acid methyl ester 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 75-36-5 acetyl chloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 105900-59-2 methyl 3-acetamido-3-phenylpropanoate 
• 67654-57-3 methyl (S)-3-acetylamino-3-phenylpropionate 
• 136744-88-2 (E)-methyl 3-acetamido-3-phenyl-2-propenoate 
• 67654-57-3 methyl (R)-3-acetamido-3-phenylpropanoate 
• 136744-90-6 (R)-(+)-methyl 3-N-methylacetamido-3-phenylpropanoate 
• 136744-90-6 (S)-3-(Acetyl-methyl-amino)-3-phenyl-propionic acid methyl ester 
• 136744-90-6 methyl 3-N-methylacetamido-3-phenylpropanoate 
• 136744-83-7 (Z)-methyl 3-N-methylacetamido-3-phenyl-2-propenoate 
• 136744-94-0 3-ethylamino-3-phenyl-1-propanol 
• 136744-96-2 (R)-3-N-methylacetamido-3-phenyl-1-propanol 
• 136744-95-1 (R)-3-methylamino-3-phenyl-1-propanol 
• 3618-96-0 (S)-N-acetylphenylalanine 
• 136744-84-8 (E)-methyl 3-N-methylacetamido-3-phenyl-2-propenoate 

Relevant academic research and scientific papers

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

Arylations of substituted enamides by aryl iodides: Regio- and stereoselective synthesis of (z)-β-amido-β-arylacrylates

Arylations of substituted enamides by aryl iodides were achieved for the first time via an unusual PdCl2(COD)/Ag3PO4 catalytic system. A broad range of (Z)-β-amido-β-arylacrylates were prepared regio- and stereoselectively in a highly efficient manner.

Enantioselective hydrogenation of β-dehydroamino acids on a cinchonidine-modified palladium catalyst

Enantioselective hydrogenation of (Z)-β-dehydroamino acids on a cinchonidine-modified Pd/Al2O3 catalyst was explored. Comparative studies by using (Z)-β-dehydroamino acids and esters identified that the carboxylic group in dehydroamino acids was essentially important to get enantioselectivities (33% for aryl substituted and 46% for alkyl substituted β-dehydroamino acids). This result extended the range of enantioselective hydrogenation of α,β-unsaturated carboxylic acids on chirally modified Pd catalysts and offered a new approach to synthesize optically active β-amino acids.

STEREOSELECTIVE SYNTHESIS OF HIGHLY SUBSTITUTED ENAMIDES

The disclosure provides new methods for the oxidative Heck cross-coupling reaction with electron-rich alkenes such as substituted β-amidoacrylate and other related substituted enamides. Previously, functionalization of enamides under Heck conditions has b

Stereochemistry and mechanism of a microbial phenylalanine aminomutase

The stereochemistry of a phenylalanine aminomutase (PAM) on the andrimid biosynthetic pathway in Pantoea agglomerans (Pa) is reported. PaPAM is a member of the 4-methylidene-1H-imidazol-5(4H)-one (MIO)-dependent family of catalysts and isomerizes (2S)-α-phenylalanine to (3S)-β-phenylalanine, which is the enantiomer of the product made by the mechanistically similar aminomutase TcPAM from Taxus plants. The NH2 and pro-(3S) hydrogen groups at Cα and Cβ, respectively, of the substrate are removed and interchanged completely intramolecularly with inversion of configuration at the migration centers to form β-phenylalanine. This is a contrast to the retention of configuration mechanism followed by TcPAM.

Stereoselective synthesis of highly substituted enamides by an oxidative heck reaction

Functionalization of enamides under Heck conditions has been limited to those with unsubstituted vinyl groups. By tuning reaction parameters that allow for the balance between stability and reactivity of reactants, the oxidative Heck cross-coupling to produce highly substituted enamides in good to excellent yields was achieved (see scheme). Copyright

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.

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

A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of β-aryl-β-amino acids by asymmetric hydrogenation

Excellent enantioselectivities and reactivities were observed in the hydrogenation of a variety of methyl (Z)-β-aryl-β-(acetyl-amino)acrylates in the presence of a rhodium catalyst with the chiral ligand binapine (see scheme). This bisbinaphthophosphepine

Highly effective chiral ortho-substituted BINAPO ligands (o-BINAPO): Applications in Ru-catalyzed asymmetric hydrogenations of β-aryl-substituted β-(acylamino)acrylates and β-keto esters

A novel family of chiral ortho-substituted BINAPO ligands (o-BINAPO) were synthesized from BINOL, and their Ru complexes were highly efficient catalysts for asymmetric hydrogenation of β-aryl-substituted β-(acylamino)acrylates and β-aryl-substituted β-keto esters. The Ru-bisphosphinite catalysts can tolerate an E/Z mixture of β-aryl-substituted β-(acylamino)acrylates. These highly enantioselective hydrogenations provide a useful way to prepare β-aryl-substituted β-amino acids and β-hydroxyl acids. Copyright