7148-01-8

Upstream product

• 2674-04-6 diphenyl cadmium 
• 1490-25-1 succinic acid monomethylester chloride 
• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 
• 77-78-1 dimethyl sulfate 
• 104-88-1 4-chlorobenzaldehyde 
• 292638-85-8 acrylic acid methyl ester 
• 99-91-2 para-chloroacetophenone 
• 29582-39-6 (E)-4-oxo-4-(4-chloro-phenyl)-but-2-enoic acid 
• 32149-26-1 (E)-methyl 4-(4-chlorophenyl)-4-oxobut-2-enoate 
• 922-67-8 propynoic acid methyl ester 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 108-90-7 chlorobenzene 

Downstream Products

• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 
• 18410-18-9 γ-(4-chlorophenyl)-γ-butyrolactone 
• 137575-62-3 1-(4’-chlorophenyl)butan-1,4-diol 
• 138745-86-5 methyl 4-(4-chlorophenyl)-4-hydroxybutanoate 
• 99822-65-8 C₁₁H₉ClO₃ 
• 1609986-11-9 methyl 4-(4-chlorophenyl)-2-(2,3-dioxoindolin-1-yl)-4-oxobutanoate 
• 1578230-26-8 (S)-methyl 4-(4-chlorophenyl)-2-(2,3-dioxoindolin-1-yl)-4-oxobutanoate 

Relevant academic research and scientific papers

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Transition Metal-Free Alkyne-Aldehyde Reductive C?C Coupling trough Cascade Borylation/Olefin Isomerization

A direct approach to γ-keto esters through cascade alkyne-aldehyde reductive C?C coupling of propargyl esters and aromatic aldehydes under transition-metal-free (TM-free) fashion was developed. Compared with multistep processes, this procedure provides a

Biocatalytic Asymmetric Reduction of γ-Keto Esters to Access Optically Active γ-Aryl-γ-butyrolactones

An efficient stereoselective syntheses of a series of functionalized optically active γ-aryl-γ-butyrolactones is achieved by enzymatic asymmetric reduction of the corresponding sterically demanding γ-keto esters employing wild-type and recombinant alcohol dehydrogenases. The best stereoselectivities for the reduction via hydrogen transfer was obtained with two short chain dehydrogenases (SDRs) of complementary stereospecificity from Aromatoleum aromaticum, namely the Prelog-specific NADH-dependent (S)-1-phenylethanol dehydrogenase [(S)-PED] and the anti-Prelog-specific (R)-1-(4-hydroxyphenyl)-ethanol dehydrogenase [(R)-HPED], respectively.Biotransformations catalyzed by both enzymes, followed by TFA-catalyzed cyclization of the resulting γ-hydroxy esters, furnished the respective (S)- and (R)-configured products with exquisite optical purity (up to >99% ee). The synthetic value was demonstrated on preparative scale for the asymmetric bioreduction of the model compound, methyl 4-oxo-4-phenylbutanoate, affording optically pure (S)-γ-phenyl-γ-butyrolactone (>99% ee) in 67–74% isolated yield at 89–95% conversion depending on the applied scale. (Figure presented.).

1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality

Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides

Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.

Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions

N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.

Organoselenium-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles

A new and efficient approach for the synthesis of oxygen and nitrogen heterocycles by organoselenium catalysis has been developed. The exo-cyclization proceeded smoothly under mild conditions with good functional group tolerance and excellent regioselectivity. Mechanistic studies revealed that 1-fluoropyridinium triflate is key for oxidative cyclization.

Remote activation of the nucleophilicity of isatin

The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.