30768-83-3

Upstream product

• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 
• 134-81-6 benzil 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 292638-85-8 acrylic acid methyl ester 
• 100-52-7 benzaldehyde 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 2680-03-7 N,N-Dimethylacrylamide 
• 2495-35-4 benzylacrylate 
• 93321-38-1 5,6-diphenyl-3,4-dihydro-2H-pyran-2-one 
• 451-40-1 phenyl benzyl ketone 
• 4258-42-8 methyl 5-oxo-4,5-diphenylpentanoate 
• 4258-41-7 5-oxo-4,5-diphenylpentanoic acid 

Relevant academic research and scientific papers

Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones

Functionalized γ-butyrolactones are privileged structures in the field of medicinal chemistry; they are found in numerous natural products and synthetic compounds with diverse biological activities. The oxidative ring contraction of 3,4-dihydropyran-2-one derivatives represents a promising yet underappreciated strategy to access these compounds. To the best of our knowledge, very few examples of this strategy have been reported, with limited investigation of the influence of stereogenic centers on the starting dihydropyranones. We investigated the iodine(III)-mediated contraction of a representative set of dihydropyranone derivatives. The method gives rapid access to functionalized γ-butyrolactones in good yields. The reaction scope was investigated, and the method was found to support various levels of substituents, even enabling access to sterically congested quaternary centers. The stereoselectivity was investigated using chiral substrates and a chiral iodine(III) reagent.

Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C?C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C?C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.

N-Heterocyclic carbene catalyzed tail-to-tail oligomerization of N,N-dimethylacrylamide (DMAA) and the search for the Stetter reaction of DMAA with benzaldehyde

The tail-to-tail oligomerization of N,N-dimethylacrylamide catalyzed by N-heterocyclic carbenes (NHCs) was investigated, giving the dimerization and trimerization products in a moderate combined yield. Reaction intermediates involved in the new oligomerization have been observed by NMR and ESI-MS. We showed the first NHC-catalyzed cross coupling of methyl methacrylate and N,N-dimethylacrylamide, and the reaction of benzaldehyde/benzoin with N,N-dimethylacrylamide.

Poly(4-vinylimidazolium) iodides: A highly recyclable organocatalyst precursor for benzoin condensation reaction

The development of highly efficient, recyclable poly(4-vinylimidazolium) iodides (2) for the benzoin condensation reaction under mild reaction conditions is discussed: poly(4-vinyl N-heterocyclic carbene)s (3) obtained from 2 showed higher catalytic activity than monomeric 4-vinyl N-heterocyclic carbene and could be successfully recovered and reused over seven times without loss of performance. the Partner Organisations 2014.

Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ- butyrolactones

Under the conditions of ruthenium(0)-catalyzed hydrohydroxyalkylation, vicinal diols 1a-1l and methyl acrylate 2a are converted to the corresponding lactones 3a-3l in good to excellent yield. The reactions of methyl acrylate 2a with hydrobenzoin 1f, benzoin didehydro-1f, and benzil tetradehydro-1f form the same lactone 3f product, demonstrating that this process may be deployed in a redox level-independent manner. A variety of substituted acrylic esters 2a-2h participate in spirolactone formation, as illustrated in the conversion of N-benzyl-3-hydroxyoxindole 1o to cycloadducts 4a-4h. Hydrohydroxyalkylation of hydroxyl-substituted methacrylate 2i with diols 1b, 1f, 1j, and 1l forms α-exo-methylene-γ-butyrolactones 5b, 5f, 5j, and 5l in moderate to good yield. A catalytic cycle involving 1,2-dicarbonyl-acrylate oxidative coupling to form oxaruthenacyclic intermediates is postulated. A catalytically competent mononuclear ruthenium(II) complex was characterized by single-crystal X-ray diffraction. The influence of electronic effects on regioselectivity in reactions of nonsymmetric diols was probed using para-substituted 1-phenyl-1,2-propanediols 1g, 1m, and 1n and density functional theory calculations.

One-step assembly of functionalized γ-butyrolactones from benzoins or benzaldehydes via an N-heterocyclic carbene-mediated tandem reaction

(Chemical Equation Presented) We describe here a direct, efficient, one-step construction of γ,γ-difunctionalized γ-butyrolactones from benzoins or benzaldehydes via a tandem reaction promoted by 1,3-dimethyl imidazolin-2-ylidene, an N-heterocyclic carbene (NHC).

Ru3(CO)12-Catalyzed intermolecular cyclocoupling of ketones, alkenes or alkynes, and carbon monoxide. [2 + 2 + 1] Cycloaddition strategy for the synthesis of functionalized γ-butyrolactones

The ruthenium-catalyzed intermolecular cyclocoupling of ketones (or aldehydes), alkenes (or alkynes), and CO, which leads to γ-butyrolactones, is described. The reaction represents the first example of the catalytic synthesis of heterocycles via an interm