133153-67-0

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 75-52-5 nitromethane 
• 611-73-4 Benzoylformic acid 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 

Downstream Products

• 199107-84-1 ethyl 3-nitro-2-phenylpropanoate 
• 1070238-04-8 (S)-ethyl 3-nitro-2-phenylpropanoate 
• 1312749-68-0 (R)-ethyl 3-nitro-2-phenylpropanoate 
• 923271-74-3 ethyl (Z)-2-phenyl-3-nitroacrylate 

Relevant academic research and scientific papers

Catalytic asymmetric Henry reactions - A simple approach to optically active β-nitro α-hydroxy esters

The development and potential of a catalytic enantioselective Henry reaction of nitromethane with various α-keto esters catalyzed by chiral bisoxazoline-copper(II) complexes are presented.

Asymmetric bioreductions of β-nitro acrylates as a route to chiral β2-amino acids

(Chemical Equation Presented) Reductions of β-nitroacrylates by Saccharomyces carlsbergensis old yellow enzyme is the key step in a concise route to optically active β2-amino acids. The enzymatic reductions occur with 87-96% ee, with larger sub

Copper-Catalyzed Cross-Dehydrogenative Coupling of α-Hydroxy Esters with Nitromethane

An efficient copper-catalyzed tandem oxidation/nitroaldol reaction of hydroxyl compounds with nucleophiles is developed. In this work, -nitro-hydroxy esters were prepared via cross-dehydrogenative coupling reaction using -hydroxy esters as hydroxy compounds and nitromethane as a nucleophile. The reaction is believed to undergo an oxidation of the hydroxyl group and then an addition of the generated carbonyl group. It is an example of CDC reactions related to hydroxyl compounds via carbonyl intermediates.

First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates

The first highly chemo- and enantioselective hydrogenation of β-nitroacrylates was accomplished with an iridium catalyst (Ir-4) with yields and enantioselectivities of up to 96% and 98% ee, respectively. The resulting α-chiral β-nitro propionates are attractive building blocks for the synthesis of chiral β2-amino acids, which are the core scaffolds of bioactive natural products, pharmaceuticals, and β-peptides.

Asymmetric friedel-crafts alkylation of α-substituted β-nitroacrylates: Access to β2,2-amino acids bearing indolic all-carbon quaternary stereocenters

A highly enantioselective Friedel-Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2-bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and tetrahydro-β-carboline through nitro reduction and sequential Pictet-Spengler cyclization was exemplified.

Peptide-catalyzed stereoselective conjugate addition reactions generating all-carbon quaternary stereogenic Centers

A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β-disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ-Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products. Copyright

Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins

This paper focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action is supported by mechanistic investigations.

Enantioselective nitroaldol reaction of α-keto esters catalyzed by a copper(II)-bisoxazolidine complex

A wide range of aliphatic and aromatic -keto esters has been transformed to α-hydroxy-β-nitro esters via the Cu(II)-bisoxa-zolidine-catalyzed Henry reaction. In the presence of 10 mol% of the chiral catalyst, nitroaldol products were obtained in up to 95% yield and 76% ee.

Dual-reagent organocatalysis with a phosphine and electron-deficient alkene: application to the Henry reaction

Triphenylphosphine in combination with methyl acrylate was found to be able to catalyze the Henry (nitroaldol) reaction of various aldehydes and α-keto esters to give the corresponding β-nitroalkanols in good to excellent yields, and a catalytic cycle involving a zwitterionic phosphine-alkene adduct was proposed for this dual-reagent organocatalysis according to the deuterium-labeling experiments with CD3NO2.

Organocatalytic asymmetric transferhydrogenation of β-nitroacrylates: Accessing β2-amino acids

We describe a highly efficient and enantioselective Hantzsch ester mediated conjugate reduction of β-nitroacrylates that is catalyzed by a Jacobsen thiourea catalyst as a key step in a new route to optically active β2-amino acids. Copyright