61598-01-4

Upstream product

• 611-73-4 Benzoylformic acid 
• 108-93-0 cyclohexanol 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 68756-65-0 cyclohexyl 2-hydroxyl-2-phenylacetate 
• 13665-04-8 2,2-dibromoacetophenone 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 1074-12-0 phenylglyoxal hydrate 
• 68484-72-0 cyclohexyl 2-phenylacetimidate hydrochloride 
• 140-29-4 phenylacetonitrile 
• 611-71-2 MANDELIC ACID 

Downstream Products

• 74956-30-2 2,3-Diphenyl-weinsaeure-dicyclohexylester 
• 64201-09-8 3-isopropyl-2,2-dimethyl-5-phenyl-oxazolidin-4-one 
• 87419-20-3 3,4-diphenyl-1-ethyl-3-hydroxyazetidin-2-one 
• 87419-20-3 3,4-diphenyl-1-ethyl-3-hydroxyazetidin-2-one 
• 87419-21-4 3,4-diphenyl-3-hydroxy-1-isopropylazetidin-2-one 
• 87419-21-4 3,4-diphenyl-3-hydroxy-1-isopropylazetidin-2-one 
• 87419-22-5 3,4-diphenyl-1-(t-butyl)-3-hydroxyazetidin-2-one 
• 87419-22-5 3,4-diphenyl-1-(t-butyl)-3-hydroxyazetidin-2-one 
• 87419-18-9 3,4-diphenyl-3-hydroxy-1-(p-methylbenzyl)azetidin-2-one 
• 87419-18-9 3,4-diphenyl-3-hydroxy-1-(p-methylbenzyl)azetidin-2-one 
• 87419-19-0 3,4-diphenyl-1-(p-chlorobenzyl)-3-hydroxyazetidin-2-one 
• 87419-19-0 3,4-diphenyl-1-(p-chlorobenzyl)-3-hydroxyazetidin-2-one 
• 87419-14-5 1-benzyl-3-hydroxy-4-(p-methylphenyl)-3-phenylazetidin-2-one 
• 87419-14-5 1-benzyl-3-hydroxy-4-(p-methylphenyl)-3-phenylazetidin-2-one 

Relevant academic research and scientific papers

Copper(I)-catalyzed aerobic oxidation of α-diazoesters

A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.

Highly adequate oxidative esterification of α-carbonyl aldehydes with alkyl halides in TBAI/TBHP mediated system

An efficient and viable synthesis of α-ketoesters from alkyl halides and α-carbonyl aldehydes has been reported under metal-free conditions. The present method involves oxidative esterification of α-carbonyl aldehydes with alkyl halide using TBAI as a promoter and TBHP as an oxidant to form α-ketoesters in good to excellent yields with versatile structural diversity. Use of commercially accessible and inexpensive substrates, broad substrate scope and good functional group tolerance are the key features of this protocol.

ZnO nanoparticles: An efficient catalyst for transesterification reaction of α-keto carboxylic esters

Pure ZnO nanoparticles were synthesized by a sustainable precipitation method using zinc nitrate and sodium hydroxide in aqueous medium at room temperature. They were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM-EDX), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV–vis) spectroscopy and Brunauer-Emmett-Teller (BET) analysis. The XRD patterns indicate the formation of the hexagonal wurtzite phase with high purity and SEM-EDS analysis confirm the purity and a homogenous distribution of the nanostructures. The ZnO nanostructures present plate-like agglomerates, resulting in a quasi-spherical morphology. The catalytic activity of the formed ZnO nanoparticles was evaluated towards the transesterification reaction of different carboxylic esters in the presence of various alcohols. This catalyst is highly selective for the transesterification of α-keto carboxylic ester (methyl benzoylformate) and leads to ca. 97percent of product yield within 24 h of reaction time.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling

A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).

Copper catalyzed photoredox synthesis of α-keto esters, quinoxaline, and naphthoquinone: Controlled oxidation of terminal alkynes to glyoxals

Herein, we report a facile visible light induced copper catalyzed controlled oxidation of terminal CC alkynes to α-keto esters and quinoxalines via formation of phenylglyoxals as stable intermediates, under mild conditions by using molecular O2 as a sustainable oxidant. The current copper catalysed photoredox method is simple, highly functional group compatible with a broad range of electron rich and electron poor aromatic alkynes as well as aliphatic alcohols (1°, 2° and 3° alcohols), providing an efficient route for the preparation of α-keto esters (43 examples), quinoxaline and naphthoquinone with higher yields than those in the literature reported thermal processes. Furthermore, the synthetic utility of the products has been demonstrated in the synthesis of two biologically active molecules, an E. coli DHPS inhibitor and CFTR activator, using the current photoredox process. In addition, we applied this methodology to the one-pot synthesis of a heterocyclic compound (quinoxaline, an FLT3 inhibitor) by trapping the intermediate phenylglyoxal with O-phenylenediamine. The intermediate phenylglyoxal can also be isolated and further reacted with an internal alkyne to form naphthoquinone. This process can be readily scaled up to the gram scale.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

Metal-free oxidative esterification of acetophenones with alcohols: A facile one-pot approach to α-ketoesters

A novel and efficient oxidative esterification method for the synthesis of α-ketoesters has been developed under mild and environmentally benign conditions, which is a facile one-pot approach to α-ketoesters from commercially available acetophenones with alcohols, especially under metal-free conditions, with broad substrate scope. A possible mechanism is proposed on the basis of a series of control experiments and DMSO18 isotopic labelling experiments.

Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds

Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.

Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines

A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.