50598-37-3

Upstream product

• 98-83-9 isopropenylbenzene 
• 151990-53-3 3-methyl-3-phenylcyclobutan-1-one 
• 136527-27-0 2,2-dichloro-3-methyl-3-phenylcyclobutan-1-one 
• 34713-70-7 2-Phenylpropanal 
• 823213-58-7 4-chloro-3,N,N-trimethyl-3-phenyl-4-(p-tolylsulfinyl)butanamide 
• 209391-69-5 (Z)-1-[(1-chloro-2-phenylprop-1-en-1-yl)sulfinyl]-4-methylbenzene 
• 209391-68-4 (E)-1-[(1-chloro-2-phenylprop-1-en-1-yl)sulfinyl]-4-methylbenzene 
• 823213-94-1 4-methyl-4-phenyl-5-(p-tolylsulfanyl)dihydrofuran-2-one 
• 52398-46-6 3-Methyl-4-oxo-3-phenyl-butyric acid methyl ester 

Downstream Products

• 313219-82-8 3-[1-Dimethylamino-meth-(Z)-ylidene]-4-methyl-4-phenyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.

Lactonization reactions through hydrolase-catalyzed peracid formation. Use of lipases for chemoenzymatic Baeyer-Villiger oxidations of cyclobutanones

A one-pot chemoenzymatic method has been described for the synthesis of γ-butyrolactones starting from the corresponding ketones through a Baeyer-Villiger reaction. The approach is based on a lipase-catalyzed perhydrolysis for the formation of peracetic acid, which is the responsible for the ketone oxidation. Optimization studies have been performed in the oxidation of cyclobutanone, finding Candida antarctica lipase type B, ethyl acetate and urea-hydrogen peroxide complex as the best system. The relative ratio of these reagents has also been analyzed in depth. This synthetic approach has been successfully extended to a family of 3-substituted cyclobutanones in high substrate concentration, yielding the corresponding lactones with excellent isolated yields and purities, under mild reaction conditions and after a simple extraction protocol.

METHOD FOR MANUFACTURING ESTER

The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ε-caprolactone was obtained at an isolated yield of 82%.

Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst

Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.

Baeyer-villiger oxidation and oxidative cascade reactions with aqueous hydrogen peroxide catalyzed by lipophilic Li[B(C6F5) 4] and Ca[B(C6F5)4]2

Efficient and selective: Two lipophilic catalysts were used for Baeyer-Villiger (BV) oxidations to give lactones in high yields (see scheme). Cascade reactions involving this BV oxidation were used to selectively obtain either unsaturated carboxylic acids or hydroxylactones in high yields from β-silyl cyclohexanones. Copyright

Palladium-catalyzed, asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones with PHOX ligands

Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center.

A new synthesis of amides and γ-lactones based on the conjugate addition of lithium enolate of amides to 1-chlorovinyl p-tolyl sulfoxides

Reaction of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones or aldehydes, with lithium enolate of N,N-dimethylacetamide gave the adducts in good to quantitative yields. The adducts were converted to

Formation of 9,10-unsaturation in the mitomycins: Facile fragmentation of β-alkyl-β-aryl-α-oxo-γ-butyrolactones

(matrix presented) A facile fragmentation of β-alkyl-β-aryl-α-oxo-γ-butyrolactones is reported. A study to assist in the elucidation of the mechanism of the reaction is also revealed.