18632-39-8

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 65-85-0 benzoic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 28383-65-5 ethyl 2-diazo-3-oxo-3-phenylpropanoate 
• 14904-52-0 ethyl 2-acetoxy-3-oxo-3-phenylpropanoate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 3885-45-8 ethyl 2,3-dioxo-3-phenylpropanoate 
• 56503-11-8 ethyl (3R)-2,3-dihydroxy-3-phenylpropanoate 
• 134390-45-7 3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester 

Relevant academic research and scientific papers

Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N?H Carbene Insertions

Implementing catalytic organometallic transformations in living settings can offer unprecedented opportunities in chemical biology and medicine. Unfortunately, the number of biocompatible reactions so far discovered is very limited, and essentially restricted to uncaging processes. Here, we demonstrate the viability of performing metal carbene transfer reactions in live mammalian cells. In particular, we show that copper (II) catalysts can promote the intracellular annulation of alpha-keto diazocarbenes with ortho-amino arylamines, in a process that is initiated by an N-H carbene insertion. The potential of this transformation is underscored by the in cellulo synthesis of a product that alters mitochondrial functions, and by demonstrating cell selective biological responses using targeted copper catalysts. Considering the wide reactivity spectrum of metal carbenes, this work opens the door to significantly expanding the repertoire of life-compatible abiotic reactions.

Metal-free α-hydroxylation of α-unsubstituted β-oxoesters and β-oxoamides

A direct metal-free α-hydroxylation of α-unsubstituted β-oxoesters and β-oxoamides was developed using m-chloroperbenzoic acid as the oxidant. This transformation enabled straightforward metal-free access to important α-hydroxy-β-dicarbonyl moieties under

DDQ-mediated oxidation of sp3 C-H bond for the direct synthesis of vicinal tricarbonyl compounds Dedicated to academician Li-Xin Dai on the occasion of his 90th birthday

A facile and direct synthetic method was developed for the construction of vicinal tricarbonyl compounds (VTCs) in moderate to excellent yields (46-92%), by treating the readily available 1,3-dicarbonyl compounds with 2,2,6,6-tetramethylpiperidine-1-oxyl

Selective catalytic oxidation of alcohols, aldehydes, alkanes and alkenes employing manganese catalysts and hydrogen peroxide

The manganese-containing catalytic system [MnIV,IV 2O3(tmtacn)2]2+ (1)/carboxylic acid (where tmtacn=N,N′,N′′-trimethyl-1,4,7-triazacyclononane), initially identified for the cis-dihydroxylation and epoxidation of alkenes, is applied for a wide range of oxidative transformations, including oxidation of alkanes, alcohols and aldehydes employing H2O2 as oxidant. The substrate classes examined include primary and secondary aliphatic and aromatic alcohols, aldehydes, and alkenes. The emphasis is not primarily on identifying optimum conditions for each individual substrate, but understanding the various factors that affect the reactivity of the Mn-tmtacn catalytic system and to explore which functional groups are oxidised preferentially. This catalytic system, of which the reactivity can be tuned by variation of the carboxylato ligands of the in situ formed [MnIII,III 2(O)(RCO2)2(tmtacn)2]2+ dimers, employs H2O2 in a highly atom efficient manner. In addition, several substrates containing more than one oxidation sensitive group could be oxidised selectively, in certain cases even in the absence of protecting groups. Copyright

A simple and highly selective biomimetic oxidation of alcohols and epoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water

A simple, mild and highly efficient biomimetic oxidation of various alcohols and epoxides with N-bromosuccinimide (NBS) catalyzed by β-cyclodextrin in water has been developed. A series of alcohols and epoxides were oxidized selectively at room temperature in excellent yields. This method is a direct one-pot synthesis under mild conditions using water as solvent and has many advantages over the existing methodologies.

Studies on dioxirane chemoselectivity: The oxidation of an enamino moiety present in a Fischer carbene complex

The dimethyldioxirane (DMD) promoted oxidative decomplexation of Fischer carbene complex 1, which contains a conjugated enamino moiety, was investigted. Thus, treatment of 1 with 3 molecular equivalents of DMD afforded a 52% yield of amide 3 as unique isolable organic product. When the reaction was performed with 1 molecular equivalent of DMD the formation of the enol intermediate 15 was evidenced by its capture as the tetrafluoroboric acid salt 16. This salt was unstable and when it was exposed to air gave rise to amide 3 and to low amounts of ethyl benzoate and acetophenone. These results indicate that the presence of an enamino group conjugated to the Fischer carbene moiety inverts the chemoselectivity previously observed in the DMD promoted decomplexation of these compounds. Thus, the major pathway involves the oxidation of the enamino double bond through the formation of an enol intermediate which reacts with oxygen to give products resulting from the breakdown of the molecule.