64498-08-4

Upstream product

• 859197-71-0 phenyl-n-butylmalonic acid 
• 7155-21-7 diethyl phenyl-n-butylmalonate 
• 60972-86-3 2-phenylhexanoyl chloride 
• 103-82-2 phenylacetic acid 
• 24716-09-4 2-phenylhexanoic acid 
• 83-13-6 diethyl 2-phenylmalonate 

Downstream Products

• 1185154-71-5 (S)-3-butyl-3-phenylindolin-2-one 
• 1186533-36-7 (3S,4S)-3-butyl-4-(4-chlorophenyl)-3-phenyl-4-(trifluoromethyl)oxetan-2-one 
• 1189062-32-5 (R)-diethyl 3-butyl-4-oxo-3-phenyl-1,2-diazetidine-1,2-dicarboxylate 
• 1214787-20-8 (7R,8S)-7-butyl-8-(4-methoxyphenyl)-7-phenyl-7,8-dihydro-[1,3]dioxolo[4,5-g]coumarin 
• 1218772-72-5 C₂₄H₂₄O₂ 
• 1241946-76-8 4-butyl-4-phenyl-2-pyridin-2-yl-1,2-oxazetidin-3-one 
• 1227364-23-9 (R)-3-butyl-3-phenylphenanthro[9,10-b][1,4]dioxin-2(3H)-one 
• 1224225-80-2 (3R,4R)-3-butyl-4-(4-nitrophenyl)-3-phenyloxetan-2-one 
• 1224226-06-5 (2R)-2-((R)-hydroxy(4-nitrophenyl)methyl)-2-phenylhexanoic acid 

Relevant academic research and scientific papers

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.

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.

NHC-promoted asymmetric β-lactone formation from arylalkylketenes and electron-deficient benzaldehydes or pyridinecarboxaldehydes

A chiral NHC catalyzes the asymmetric formal [2 + 2] cycloaddition of alkylarylketenes with both electron-deficient benzaldehydes and 2- and 4-pyridinecarboxaldehydes to generate stereodefined β-lactones. In the benzaldehyde series, optimal product diastereo- and enantiocontrol is observed using 2-nitrobenzaldehyde (up to 93:7 dr (syn:anti) and 93% ee). Substituted 2- and 4-pyridinecarboxaldehydes are also tolerated in this process, generating the corresponding β-lactones in good yield and enantioselectivity, although the diastereocontrol in these processes is highly dependent upon the aldehyde substitution. These processes are readily scalable, allowing multigram quantities of the β-lactone products to be prepared. Derivatization of these products, either through ring opening into the corresponding stereodefined β-hydroxy and β-amino acid derivatives without loss of stereochemical integrity or via cross-coupling, is demonstrated.

An asymmetric hetero-claisen approach to 3-alkyl-3-aryloxindoles

The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

Multistep one-pot wittig/nazarov reaction for construction of cyclopentenone with diazo compounds and acid chlorides

A facile multistep one-pot synthesis of single or fused cyclopentenones has been developed. The sequence involves a transition metalcatalyzed ylide formation/Wittig Olefination/Nazarov Cyclization.

N-heterocyclic carbene-mediated enantioselective addition of phenols to unsymmetrical alkylarylketenes

Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering α-alkyl-α-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phe-nylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

Chemiluminiscent Thermolysis of a Peroxylactones

A comprehensive study of the chemiluminiscent decomposition of a three α-peroxylactones (dimethyl α-peroxylactone (1), phenyl n-butyl α-peroxylactone (2), and diphenyl α-peroxylactone (3)) has been undertaken.Each compound decomposes to yield CO2 and the corresponding ketone in a high yield.The chemiluminiscent species produced in these reactions have been characterized by a number of different measurements including distribution of direct chemiluminiscence, lifetimes, energy transfer, activation parameters, and photochemical reactions.Excited state chemiexcitation efficiences have also been evaluated.It is shown that a combination of conventional kinetic measurements and "step analysis" of the chemiluminiscence intensivity provides a means of evaluating the activation energies for the deactivation paths of electronically excited states that precede the emission step responsible for chemiluminiscence.The latter activation energies may also be monitored directly in some cases by measurement of excited-state lifetimes as a function of temperature.The agreement between the activation energies generated from chemiluminiscence data and direct photoexcitation measurements is within the experimental error.The results for 1 are compared to those for tetramethyldioxetane (4) (both produce electronically excited acetone) and are found to be in excellent agreement.