3156-07-8

Upstream product

• 32346-08-0 (1-methoxy-2-phenylprop-1-enyloxy)trimethylsilane 
• 25145-43-1 2-phenylpropionyl chloride 
• 60-29-7 diethyl ether 
• 71506-74-6 2-chloro-2-phenyl-propionyl chloride 
• 74097-41-9 trans-3,5-dihydro-3,5-dimethyl-3,5-diphenyl-4H-pyrazol-4-one 
• 492-37-5 hydratropic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 3893-35-4 1-diazo-1-phenyl-2-propanone 
• 22293-10-3 (1-diazoethyl)benzene 
• 4371-02-2 2-methyl-2-phenylmalonic acid 
• 525-06-4 diphenyl ketene 
• 515-30-0 2-phenyllactic acid 
• 31508-44-8 2-phenylpropionic acid methyl ester 

Downstream Products

• 40195-51-5 2,4-dimethyl-2,4-diphenyl-cyclobutane-1,3-dione 
• 59983-38-9 (S)-1,3-diphenylbutan-2-one 
• 67504-36-3 (R)-1,3-diphenylbutan-2-one 
• 103185-03-1 1-(4-methoxyphenyl)-2-phenyl-2-propen-1-one 
• 97234-80-5 (Z)-2-phenyl-3-trimethylsilyloxy-2-heptene 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 88641-61-6 2-phenylpropionic butyl ester 
• 117760-34-6 1-methylvinyl 2-phenylpropanoate 
• 117760-43-7 2,2-Dimethyl-6-phenyl-heptane-3,5-dione 
• 117760-35-7 1-t-butylvinyl 2-phenylpropanoate 
• 155397-68-5 4-Methyl-2-phenyl-5-hexen-3-on 
• 127302-44-7 (S)-5-phenyl-1-hexen-4-one 
• 141515-81-3 (R)-5-phenyl-1-hexen-4-one 
• 80720-86-1 α-phenylethyl 2-phenylpropanoate 

Relevant academic research and scientific papers

Construction of All-Carbon Quaternary Stereocenters via Sequential Photoactivation/Isothiourea Catalysis

Highly enantioselective [4 + 2] cyclizations of azadienes with in situ generated ketenes were developed through sequential visible-light photoactivation/isothiourea catalysis, which offers a novel approach for the creation of all-carbon quaternary stereoc

Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes

Higher-order cycloadditions, particularly [8+2] cycloadditions, are a straightforward and efficient strategy for constructing significant medium-sized architectures. Typically, configuration-restrained conjugated systems are utilized as 8π-components for

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids

The asymmetric synthesis of β2,2-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2-amino acids has been developed.

A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: An unexpected route to tetrahydrofurans

A novel sequential reaction that combines a visible light-induced Wolff rearrangement of α-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58-99% yields).

Synthesis of Chiral Esters via Asymmetric Wolff Rearrangement Reaction

The first asymmetric Wolff rearrangement reaction that directly converts α-diazoketones into broadly useful chiral α,α-disubstituted carboxylic esters with high enantioselectivities (up to 97.5:2.5 er) is reported. The cascade reaction proceeds through the seamless combination of visible-light-induced formation of the ketene intermediate and asymmetric ketene esterification using a readily available benzotetramisole-type catalyst.

Addition-Rearrangement of Ketenes with Lithium N- tert-Butanesulfinamides: Enantioselective Synthesis of α,α-Disubstituted α-Hydroxycarboxylic Acid Derivatives

Addition of the lithium salts of chiral N-substituted tert-butanesulfinamides to ketenes and subsequent silylation initiates stereoselective [2,3]-rearrangement, which affords enantioenriched α,α-disubstituted α-sulfenyloxy carboxamides through a reaction

Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral

Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94% ee) or α-chloroesters (up to 94% ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.

Origins of diastereoselectivity in lewis acid promoted ketene-alkene [2 + 2] cycloadditions

A detailed analysis of a Lewis acid promoted ketene-alkene [2 + 2] cycloaddition is reported. The studies have led to a rationalization for an observed inversion of diastereoselectivity between thermally induced and Lewis acid promoted ketene-alkene [2 + 2] cycloadditions. The model is supported with both experimental and computational results.

Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions

Described are the first examples of ketene-alkene [2 + 2] cycloadditions promoted by Lewis acids. Notable features of this method include (1) substantial rate acceleration relative to traditional thermal reactions, (2) good diastereoselectivities and yields for the formation of the cyclobutanone products, and (3) inverse diastereoselectivity compared with related thermal cycloadditions for many examples. These studies not only provide access to synthetically versatile cyclobutanones that cannot be prepared by traditional thermal cycloadditions but also address important mechanistic questions regarding ketene-alkene [2 + 2] cycloaddition reactions.

Structures and ambident reactivities of azolium enolates

Oxygen versus carbon: Azolium enolates were generated by the reactions of N-heterocyclic carbenes (NHCs) with methyl phenyl ketene and characterized by X-ray crystallography. Kinetic studies show that the enolate oxygen is 20 times more nucleophilic than