887641-60-3

Upstream product

• 35249-73-1 benzyl chlorooxalate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 1075-47-4 4-methylphenylglyoxal 
• 538-60-3 dibenzyl hydrogen phosphite 
• 100-51-6 benzyl alcohol 
• 766-97-2 4-n-methylphenylacetylene 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 100-39-0 benzyl bromide 
• 122-00-9 para-methylacetophenone 
• 1432320-49-4 benzyl 2-diazo-2-(p-tolyl)acetate 
• 39749-79-6 benzyl 2-(4-methylphenyl)ethanoate 

Downstream Products

• 66334-32-5 2-methyl-2-(4-methylphenyl)-4-oxovaleraldehyde 
• 101693-57-6 (R)-(+)-4-methyl-4-(4-methylphenyl)cyclopent-2-enone 
• 1449335-98-1 C₂₉H₂₉NO₆S 
• 1449336-17-7 C₂₃H₂₁NO₄S 
• 1416913-04-6 benzyl (R)-2-hydroxy-3-(3-oxocyclohex-1-en-1-yl)-2-(p-tolyl)propanoate 

Relevant academic research and scientific papers

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters

Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re

Chemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis

We developed a chemoselective catalytic activation of carboxylic acid for a 1e- radical process. α-Oxidation of a variety of carboxylic acids, which preferentially undergo undesired decarboxylation under radical conditions, proceeded efficiently under the optimized conditions. Chemoselective enolization of carboxylic acid was also achieved even in the presence of more acidic carbonyls. Extensive mechanistic studies revealed that the cooperative actions of iron species and alkali metal ions derived from 4 ? molecular sieves substantially facilitated the enolization. For the first time, catalytic enolization of unprotected carboxylic acid was achieved without external addition of stoichiometric amounts of Br?nsted base. The formed redox-active heterobimetallic enediolate efficiently coupled with free radical TEMPO, providing synthetically useful α-hydroxy and keto acid derivatives.

Pd(OAc)2-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

An efficient Pd(OAc)2-catalyzed asymmetric hydrogenation of α-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)2, a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)2 which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral α-arylglycine fragments are widely found in many chiral products and bioactive molecules.

In Situ Generated AgII-Catalyzed Selective Oxo-Esterification of Alkyne with Alcohol to α-Ketoester: Photophysical Study

An expert and easy one-step catalytic method for the multi O-C coupling of alkyne is developed for the synthesis of valuable α-ketoesters and their chiral analogues, in contrast to the generation of esters by a noncatalytic method. The in situ generated powerful AgII catalyst from AgOTf is the workhorse in the oxidative grafting of alkyne with PhIO and alcohol. The radical mechanism is confirmed in our controlled experiments and UV-vis study.

2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction

Highly efficient catalyst free methods for the synthesis of α-hydroxy-β-oxophosphonates and α-oxoesters have been described. The existence of a 2-oxo group in α-oxoaldehydes is a key factor in promoting the reaction of the tervalent phosphite form towards 2-oxoaldehydes in the synthesis of α-hydroxy-β-oxophosphonates. The in situ activated α-C-H atom of α-hydroxy-β-oxophosphonates sustains aerobic intramolecular nucleophilic displacement in a curious way to produce α-oxoester.

Highly chemo-, enantio-, and regioselective synthesis of α,α-disubstituted furanones by Cu-catalyzed conjugate addition

A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center. Selective chemistry: A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported (see scheme). Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place.

Enantioselective rhodium-catalyzed addition of arylboronic acids to α-ketoesters

(Chemical Figure Presented) Rhodium catalysis: The first example of a catalytic asymmetric addition of arylboronic acids to α-ketoesters was realized by using a chiral RhI-spirophosphite ligand complex in aqueous solvent to provide tertiary α-hydroxyesters in good yields with high enantioselectivities (see scheme; DCE = 1,2-dichloroethane).