20215-55-8

Upstream product

• 4405-27-0 2,2-dimethyl-4-phenyl-3-butenoic acid 
• 15116-34-4 2,2-dimethyl-4-oxo-4-phenylbutanoic acid 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 74-88-4 methyl iodide 
• 5950-19-6 3-chloro-3-methyl-2-butanone 
• 100-52-7 benzaldehyde 
• 13511-38-1 3-chloropivalic acid 
• 17347-61-4 2,2-dimethylsuccinic anhydride 
• 23092-23-1 3-methyl-1-phenylbut-3-en-1-ol 
• 62036-40-2 2-Hydroxy-3,3-dimethyl-5-phenyltetrahydrofuran 
• 96-09-3 styrene oxide 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 4374-44-1 2,2-dimethyl-4-phenylbutyric acid 
• 100-42-5 styrene 

Downstream Products

• 718627-96-4 acetic acid 3,3-dimethyl-5-phenyl-tetrahydro-furan-2-yl ester 
• 904313-97-9 3,3-dimethyl-2,5-diphenyl-tetrahydro-furan-2-ol 

Relevant academic research and scientific papers

Cu-catalyzed intermolecular oxyalkylation of styrenes under air: Access to diverse iminolactones

A practical, simple, and efficient copper-catalyzed highly regioselective oxyalkylation of styrenes and readily available α-bromoacetamides under air is realized. This reaction exhibits a wide range of functional group tolerance in styrenes and α-bromoacetamides to afford iminolactones.

Direct α-Tertiary Alkylations of Ketones in a Combined Copper–Organocatalyst System

Herein, we report an efficient method for the tertiary alkylation of a ketone by using an α-bromocarbonyl compound as the tertiary alkyl source in a combined Cu-organocatalyst system. This dual catalyst system enables the addition of a tertiary alkyl radical to an enamine. Mechanistic studies revealed that the catalytically generated enamine is a key intermediate in the catalytic cycle. The developed method can be used to synthesize substituted 1,4-dicarbonyl compounds containing quaternary carbons bearing various alkyl chains.

Erratum: Cu-Catalyzed Three-Component Carboamination of Alkenes (J. Am. Chem. Soc. (2018) 140:1 (58?61) DOI: 10.1021/jacs.7b10529)

Pages 59 and 60. We have identified an error in the structural analysis of compounds presented in our publication detailing. (Table presented).

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Visible-Light-Induced C-O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones

Visible-light-induced intramolecular C-O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway. Detailed mechanistic studies suggest that molecular oxygen is used to trap the radical intermediate to form benzyl alcohol, which undergoes cyclization. This new approach serves as a powerful platform by providing efficient access to valuable five- and six-membered cyclic ethers and lactones with a unified protocol.

Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

Cu-Catalyzed Three-Component Carboamination of Alkenes

Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphat

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids

A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.

A catalytic approach to the metal-free reaction of epoxides with ketene silyl acetals for accessing γ-lactones

The first catalytic approach to the nucleophilic addition of silyl ketene acetals 2 to epoxides 1 is reported. The defined protocol is metal-free using tetrabutylammonioum fluoride as the catalyst. It works in a very efficient manner under solvent-free co

Formation of quaternary carbon centers by highly regioselective hydroformylation with catalytic amounts of a reversibly bound directing group

Directly opposing Keulemans rule! Phosphinites work as reversibly bound directing groups allowing for the first highly regioselective hydroformylation of 3-substituted homoallylic alcohols to construct quaternary carbon centers. This method enables the at