19185-84-3

Upstream product

• 186581-53-3 diazomethane 
• 92963-95-6 (2RS,3SR)-2-benzoylamino-3-hydroxy-3-phenylpropanoic acid 
• 98-88-4 benzoyl chloride 
• 80182-99-6 β-hydroxyphenylalanine methyl ester hydrochloride 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 17193-41-8 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester; hydrochloride 
• 100-52-7 benzaldehyde 
• 69-96-5 dl-threo-phenylserine 
• 19185-45-6 methyl 2-(benzoylamido)-3-oxo-3-phenylpropionate 
• 93-97-0 benzoic acid anhydride 
• 38061-23-3 α-Phenylacyl amino acid methyl ester hydrochloride 

Downstream Products

• 19185-42-3 2-benzoylamino-3-chloro-3-phenyl-propionic acid methyl ester 
• 842-74-0 4-benzylidene-2-phenyloxazole-5(4H)-one 
• 19185-47-8 trans-2,5-diphenyl-4-methoxycarbonyl-4,5-dihydrooxazole 
• 1205-08-9 methyl hippurate 

Relevant academic research and scientific papers

Rhodium-mediated asymmetric transfer hydrogenation: A diastereo- and enantioselective synthesis of: Syn -α-amido β-hydroxy esters

The preparation of syn α-benzoylamido β-hydroxy esters through asymmetric transfer hydrogenation (ATH) with a tethered Rh(iii)-DPEN complex via dynamic kinetic resolution (DKR) has been developed for the first time starting from α-benzoylamido β-keto esters. A variety of α-benzoylamido β-keto esters were converted under mild conditions into the corresponding syn α-benzoylamino β-hydroxy esters with high yields (up to 98%) and diastereomeric ratios (up to >99:1 dr) as well as excellent enantioselectivities (up to >99% ee).

Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts-stereoselective synthesis of anti-β-hydroxy-α-amino acids

The asymmetric hydrogenation of α-amino-β-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-β-hydroxy-α-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate.

Rhodium-catalyzed asymmetric hydrogenation through dynamic kinetic resolution: asymmetric synthesis of anti-β-hydroxy-α-amino acid esters

Rhodium-catalyzed asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides through dynamic kinetic resolution is described. The hydrogenation proceeds with the catalyst derived from a Rh complex and a chiral ferrocenylphosphine under hydrogen in th

Nitrate esters in the generation of amino acid radicals

Nitrate esters, prepared by treatment of β-hydroxy-α-amino acid derivatives with nitric acid, react with tributyltin hydride to give the corresponding alkoxyl radicals. These radicals readily undergo β-scission, providing a convenient route for the regiocontrolled production of α-carbon-centred amino acid radicals. By examining the partitioning of the alkoxyl radicals between the β-scission process and the competing hydrogen transfer reaction, it has been possible to evaluate the influence of electronic and steric effects on the β-scission reaction and the formation of the carbon-centred radicals.

ASYMMETRIC SYNTHESIS OF β-HYDROXY-α-AMINO ACIDS BY CONDENSATION OF ALIPHATIC AND AROMATIC ALDEHYDES WITH ZINC(II) AND COPPER(II) COMPLEXES OF (1R)-3-HYDROXYMETHYLENE BORNAN-2-ONE GLYCINE IMINES

The stereochemical outcome of the condensation reactions of aliphatic and aromatic aldehydes with the metal complexes 1 is strongly dependent on the nature of the metal ion.The copper(II) complex 1a only affords threo-β-hydroxy-α-amino acids with fairly good enantiomeric excess when reacting with aromatic aldehydes.The zinc(II) complex 1b gives a mixture of threo and erythro diastereoisomers with a predominance of the erythro forms in the case of aromatic aldehydes.

Asymmetric Synthesis of β-Phenylserines by Condensation of Benzaldehyde with Zinc(II) and Copper(II) Complexes of (1R)-3-Hydroxymethylenebornan-2-one Glycine Imines

The condensation between benzaldehyde and the zinc(II) and copper(II) complexes of the glycine imines of (1R)-3-hydroxymethylenebornan-2-one in the presence of strong bases has been studied.The diastereo- and enantio-selectivity of the reaction together with the spectroscopic characterization of the metal complexes and the corresponding enolate intermediates are reported.