23244-37-3

Upstream product

• 10488-87-6 ethyl 2-benzoylpropionate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 32742-19-1 methyl 2-benzoylpropionate 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 21943-76-0 4-allyl-4-methyl-3-phenyl-4H-isoxazol-5-one 
• 21944-69-4 2-allyl-4-methyl-3-phenyl-2H-isoxazol-5-one 
• 107576-17-0 5-Methyl-6-oxo-4-phenyl-6H-[1,3]oxazine-2-carboxylic acid methyl ester 
• 107576-05-6 (Z)-2-(4-Methyl-5-oxo-3-phenyl-4,5-dihydro-isoxazol-4-yl)-but-2-enedioic acid dimethyl ester 
• 107575-96-2 4,4'-Dimethyl-6,6'-dioxo-5,5'-diphenyl-3,6,3',6'-tetrahydro-[2,2']bi[[1,3]oxazinyl]-2,2'-dicarboxylic acid dimethyl ester 
• 75167-71-4 4,4'-Dimethyl-3,3'-diphenyl-4H,4'H-[4,4']biisoxazolyl-5,5'-dione 
• 75167-72-5 4,4'-Dimethyl-3,3'-diphenyl-4'H-[2,4']biisoxazolyl-5,5'-dione 
• 148343-08-2 C₂₀H₂₇N₃O₆ 
• 3989-60-4 4-methyl-4-(4-nitro-phenylazo)-3-phenyl-4H-isoxazol-5-one 
• 3356-90-9 5-chloro-4-methyl-3-phenylisoxazole 
• 3477-03-0 5-bomo-4-methyl-3-phenylisoxazole 
• 10557-77-4 4-methyl-3,5-diphenylisoxazole 

Relevant academic research and scientific papers

Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles: An efficient access to trisubstituted isoxazoles

The Suzuki-Miyaura cross-coupling of 3,4-disubstituted 5-bromoisoxazoles 1 at the C5 position has successfully proceeded in the presence of Pd2(dba)3 and P(t-Bu)3·HBF4 catalysts to give the corresponding trisubstituted isoxazoles 3 in good to high yields while suppressing the formation of ketone 4 as a byproduct. The use of bulky phosphine ligand P(t-Bu)3·HBF4 is essential for the current transformation, and the formation of ketone 4, which was a major product in the previous report, was able to be suppressed under the current conditions.

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Complementing Pyridine-2,6-bis(oxazoline) with Cyclometalated N-Heterocyclic Carbene for Asymmetric Ruthenium Catalysis

A strategy for expanding the utility of chiral pyridine-2,6-bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N-heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chemistry, including ring contraction to chiral 2H-azirines (up to 97 % ee with 2000 TON) and enantioselective C(sp3)?H aminations (up to 97 % ee with 50 TON).

Asymmetric Synthesis of 2H-Azirines with a Tetrasubstituted Stereocenter by Enantioselective Ring Contraction of Isoxazoles

Highly strained 2H-azirines with a tetrasubstituted stereocenter were synthesized by the enantioselective isomerization of isoxazoles with a chiral diene–rhodium catalyst system. The effect of ligands and the coordination behavior support the proposed cat

Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

An unprecedented silver-catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom-economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds. Furthermore, the method can also be applied for the late-stage modification of a few biologically active molecules.

Regioselective catalytic asymmetric C-alkylation of isoxazolinones by a base-free palladacycle-catalyzed direct 1,4-addition

Isoxazolinones constitute a class of heterocycles utilized for the development of novel drug candidates. The cyclic oxime ester motif is also synthetically useful as it contains functional handles which have previously been used to provide access to an assortment of valuable compound classes not easily accessible by alternative approaches. However, asymmetric methods towards isoxazolinones are notoriously scarce. Herein we report the first catalytic asymmetric alkylations of isoxazolinones forming all-C-substituted quaternary stereocenters. The present studies were driven by the question of how to control the regioselectivity in the competition of different nucleophilic positions. The investigation of a direct 1,4-addition uncovered that a sterically demanding palladacycle catalyst directs the reactivity in the absence of a base nearly exclusively to the nucleophilic C atom, while at the same time it allows for high enantioselectivity and TONs up to 1900.