98184-95-3

Upstream product

• 93-59-4 Perbenzoic acid 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 17451-20-6 (E)-ethyl-2-oxo-4-phenylbut-3-enoate 
• 107969-78-8 methyl benzylidenepyruvate 
• 14371-10-9 (E)-3-phenylpropenal 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 105885-67-4 (+/-)-(3E)-1-chloro-4-phenyl-but-3-en-2-ol 
• 273212-42-3 (E)-2-[(1-Benzenesulfonyl-cyclopropyl)-dimethyl-silanyl]-4-phenyl-but-3-enoic acid ethyl ester 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 20047-19-2 (Z)-4-phenylbut-3-en-1-ol 
• 869111-33-1 (E)-4-phenylbut-3-enyl hydroxycarbamate 
• 126580-12-9 (E)-ethyl 2-diazo-4-phenylbut-3-enoate 

Downstream Products

• 206257-87-6 1-benzoyloxy-4-phenyl-E-3-butene-2-ol 
• 55177-35-0 4-phenylbut-2-enal 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 
• 112698-74-5 (E)-1-hydroxy-4-phenylbut-3-en-2-one 
• 229648-88-8 (2S,3E)-4-phenylbut-3-ene-1,2-diol 
• 505085-76-7 (2R,3E)-2-amino-4-phenylbut-3-en-1-ol 
• 206257-91-2 (S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol 
• 206257-90-1 Benzoic acid (E)-(S)-2-acetoxy-4-phenyl-but-3-enyl ester 

Relevant academic research and scientific papers

Solid-phase synthesis of dihydropyrans by Eu(fod)3-catalysed [4+2] heterocycloaddition of vinyl ethers with benzylidenepyruvic acid esters. Comparison with conventional homogeneous liquid phase conditions

The OH groups of Wang resin were esterified with benzylidenepyruvic acid (1) to give the immobilized 1-oxabutadiene 2. The latter reacted with vinyl ethers 3a-h (dienophiles) in the presence of Eu(fod)3, and the resulting adducts 4a-h underwent reductive cleavage with LiAlH4 to afford the dihydropyrans 5a-h in high (62 to 100%) overall yields. A similar sequence carried out under conventional homogeneous liquid phase conditions led to significantly lower yields. The endo/exo selectivity of the cycloaddition reaction was the same in both cases.

Intramolecular C(sp3)–H Bond Oxygenation by Transition-Metal Acylnitrenoids

This study demonstrates for the first time that easily accessible transition-metal acylnitrenoids can be used for controlled direct C(sp3)-H oxygenations. Specifically, a ruthenium catalyst activates N-benzoyloxycarbamates as nitrene precursors towards regioselective intramolecular C?H oxygenations to provide cyclic carbonates, hydroxylated carbamates, or 1,2-diols. The method can be applied to the chemoselective C?H oxygenation of benzylic, allylic, and propargylic C(sp3)?H bonds. The reaction can be performed in an enantioselective fashion and switched in a catalyst-controlled fashion between C?H oxygenation and C?H amination. This work provides a new reaction mode for the regiocontrolled and stereocontrolled conversion of C(sp3)-H into C(sp3)?O bonds.

Copper-catalyzed oxyvinylation of diazo compounds

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.

Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution

3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermo

The phenylthiocyclopropylsilyl group: A useful latent hydroxy group

The α-dimethyl(1-phenylthio)cyclopropylsilyl group was used as a new masked hydroxy group. Three procedures have been devised to allow the oxidation of this silicon group in the presence of various functionalities. The desired alcohols are obtained in high yields with retention of configuration at the carbon centre. (C) 2000 Elsevier Science Ltd.

Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1- O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting part

Olefination and hydroxymethylation of aldehydes using Knochel's (dialkoxyboryl)methylcopper reagents

The in-situ preparation of [(Me2C)2O2BCH2]Cu(CN)ZnI (3) from Knochel's (dialkoxyboryl)-methylzinc reagent (2) and CuCN·2LiCl in THF, followed by its addition to aldehyde in the presence of boron trifluoride etherate yielded rather stable β-hydroxyalkylboronates (5). The thermal dehydroxyboronation or the alkaline hydrogen peroxide oxidation of 5 gave the corresponding alkenes (6) or 1,2-alkanediols (7) in high yields. The reaction provides a simple procedure for the olefination or the hydroxymethylation of aldehydes.

The dimethyl(1-phenylthio)cyclopropylsilyl group as a masked hydroxyl group

The title group has been used as a masked hydroxyl group, allowing a mild and high yielding oxidation of the C-Si bond. Its use in various transformations demonstrates its chemical stability as well as its ability to be transformed into the corresponding OH group even in the presence of sensitive functionalities.

High Yield Endoselective Heterocycloadditions involving Benzylidenepyruvic Esters as the Heterodiene and an Alkoxystyrene as the Dienophile

The benzylidenepyruvic esters 6, 10a-d and 11 smoothly reacted with the alkoxystyrenes 12 and 13 in refluxing hexane or toluene and in the presence of catalytic amounts of Eu(fod)3, thus selectively leading to the endo adducts 14-21 in high yields.This represents the first examples of an efficient heterocycloaddition of styrene derivatives without using the high pressure technique.The above adducts are potential intermediates for sugiresinol 7 and related tetrahydropyran neolignans.

NAD(P)H MODELS 20 CHEMOSELECTIVE METAL ION CATALYZED REDUCTION OF α-KETO-β,γ-UNSATURATED ESTERS BY 1,4-DIHYDROPYRIDINE DERIVATIVES

Ethyl 2-oxo-4-aryl-3-butene-1-oates (1a-c) are reduced by NAD(P)H models (1-n-propyl-1,4-dihydronicotinamide (4) and Hantzsch ester (5)), in presence of magnesium perchlorate.One equivalent of the reductant reduces the substrates selectively to the corresponding 2-oxo-4-arylbutanoates (6, 10a, b).An additional equivalent and higher temperature, converts ethyl 2-oxo-4-phenylbutanoate (6) to ethyl 2-hydroxy-4-phenylbutanoate (7).Reduction of ethyl 2-oxo-4-phenyl-3-buten-1-oate (1a) by Hantzsch ester in C2H5OD or by Hantzsch ester-4,4-d2 in C2H5OH, leads to direct transfer of the hydrogen or deuterium, respectively, without isotopic scrambling.These results have been interpreted to support the hydride transfer mechanism.