17071-33-9

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 64-17-5 ethanol 
• 100-52-7 benzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 127039-91-2 3-methoxy(tri-n-butyltin)crotonate 
• 141-97-9 ethyl acetoacetate 
• 848900-76-5 5-(2-Chloro-acetoxy)-3-oxo-5-phenyl-pentanoic acid ethyl ester 

Downstream Products

• 107400-64-6 ethyl syn-3,5-dihydroxy-5-phenylvalerate 
• 107400-64-6 (3RS,5SR)-3,5-dihydroxy-5-phenyl-pentanoic acid ethyl ester 
• 1123850-99-6 ethyl (3R,5S)-3,5-dihydroxy-5-phenylpentanoate 
• 682770-63-4 5-butyryloxy-3-oxo-5-phenyl-pentanoic acid ethyl ester 
• 1403890-67-4 9-phenyl-1,4,8-trioxaspiro[4.5]decan-7-one 
• 848900-98-1 (5S) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 
• 848900-50-5 (5R) ethyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate 
• 871505-88-3 3-hydroxy-5-oxo-5-phenylpent-3-enoic acid ethyl ester 
• 184839-53-0 ethyl 5-hydroxy-2-diazo-3-oxo-5-phenylpentanoate 
• 1334180-39-0 ethyl 5-(allyloxy)-3-oxo-5-phenylpentanoate 
• 682770-94-1 (5S) ethyl δ-butyryloxy-δ-phenyl-β-oxo-pentanoate 
• 1503-99-7 ethyl 3-oxo-5-phenyl-4-pentenoate 
• 848900-76-5 5-(2-Chloro-acetoxy)-3-oxo-5-phenyl-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

A convenient stereoselective synthesis of 5-hydroxy-3-oxoesters and 3-hydroxy-5-oxoesters

A biocatalytic approach was employed for the asymmetric reduction of sterically demanding ketones to prepare 3-hydroxy-5-oxo-5-phenylpentanoates and 5-hydroxy-3-oxo-5-phenylpentanoates. Screening a collection of microorganisms led to the identification of

Double reformatsky reaction: Divergent synthesis of δ-hydroxy-β- ketoesters

The double Reformatsky reaction, tandem addition of two molecules of zinc alkanoate to a carbonyl compound, and its synthetic application to a series of δ-hydroxy-β-ketoesters has been developed. The key to accelerate the double Reformatsky reaction is considered to be a complex-induced proximity effect of the in situ generated zinc alkoxide coordinated with the pyridyl group of the substrate or bidentate amines. A noteworthy feature of the reaction system is its high tolerance of functional groups due to the moderate nucleophilicity of organozinc reagents and the mild reaction conditions. Moreover, spectroscopic and crystallographic analyses of the zinc complex of the double Reformatsky product support the proposed mechanism of reaction site discrimination for ketones, aldehydes, nitriles, carboxylic acid anhydrides, and esters.

Regioselective addition of 1,3-dicarbonyl dianions to carbonyl compounds: One pot lactonization and ketalization of-hydroxy-keto esters to protected pyrone derivatives

A simple and efficient strategy for the synthesis of 6-substituted-2-pyrone derivatives, by BF3OEt2 mediated one pot cyclization and keto-protection of-hydroxy-keto esters, obtained via regioselective addition of 1,3-dicarbonyl diani

Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy- β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

A simple and convenient method was reported for the preparation of optically active β-hydroxy-β-arylpropionates, δ-hydroxy-δ- aryl-β-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products.

A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxocarboxylates

Enzymatic hydrolysis was applied to the preparation of certain chiral 5-hydroxy-3-oxo-carboxylates that are potential precursors for natural product synthesis via the formation of lactone derivatives and tetrahydropyran rings.

Synthesis of 3- and 5-alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones by the condensation of β-oxo acid esters with aldehydes and ketones

A method is proposed for obtaining 3- and 5-alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones based on the condensation of the dianion of alkyl(dialkyl)acetoacetic ester with aldehydes and ketones.

Synthesis of δ-hydroxy-β-oxo esters using sonochemical Blaise reaction

A simple and convenient synthesis of δ-hydroxy-β-oxo esters starting from β-hydroxynitriles and ethyl bromoacetate using zinc under sonication is reported.

Ethyl γ-diiodosamario-β-oxobutanoates, generation by reaction of ethyl bromoacetate with samarium diiodide and synthetic applications

A treatment of ethyl bromoacetate with two molar equiv of samarium diiodide at -50 deg C produces ethyl γ-diiodosamario-β-oxobutanoate via selfcondensation of initially generated ethyl α-diiodosamarioacetate with bromoacetate, followed by the reduction of the condensate with samarium diiodide.Ethyl γ-diiodosamario-β-oxobutanoate adds to aldehydes or ketones affording δ-hydroxy-β-keto ester in excellent yields and to acid anhydrides giving δ,β-diketo esters in moderate to good yields.The reactive intermediate, ethyl γ-diodosamario-β-oxobutanoate, is stable at -50 deg C in THF but isomerizes at 0 deg C affording stable samarium acetylacetonate.

A Preparation of β-Oxoester Enolate Equivalents from SmI2 and α-Bromoalkanoates

A treatment of ethyl bromoacetate with two molar equivalent of samarium diiodide at -50 deg C for 15 min in THF produces a β-oxoester enolate equivalent; the reagent reacts with ketones or aldehydes to give δ-hydroxy-β-oxoesters in excellent yields.

TIN ANALOGS OF THE VINYLOGOUS REFORMATSKY REACTION. REGIO- AND STEREOCHEMICAL CONSIDERATIONS

Ethyl-4-(tri-n-butyltin)-3-methyl crotonate and ethyl-4-(tri-n-butyltin)-3-methoxycrotonate were condensed with benzaldehyde and cyclohexanone.The regio- and stereochemical profiles were determined in an effort to control the course of dienolate additions