69916-33-2

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 4392-24-9 Cinnamyl bromide 
• 64393-47-1 ethyl 2-acetyl-3-phenyl-4-pentenoate 
• 141-97-9 ethyl acetoacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 300-57-2 allylbenzene 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 85217-69-2 cinnamyl methyl carbonate 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 103-54-8 cinnamyl acetate 
• 100-52-7 benzaldehyde 
• 4192-77-2 ethyl cinnamate 
• 2723-42-4 ethyl 3-pyrrolidinobut-2-enoate 

Downstream Products

• 1615240-26-0 ethyl 2-cinnamyl-3-methyl-2H-azirine-2-carboxylate 
• 1615240-06-6 C₂₂H₂₅NO₅S 
• 1615239-86-5 C₁₅H₁₉NO₃ 
• 1702-14-3 ethyl 2-methyl-6-phenylnicotinate 
• 82194-04-5 (E)-6-Phenyl-5-hexen-2-one oxime 
• 61478-38-4 1t-phenyl-hexen-⁽¹⁾-one-⁽⁵⁾-semicarbazone 
• 851108-01-5 2-methyl-3-[(2E)-3-phenylprop-2-enyl]quinolin-4-ol 

Relevant academic research and scientific papers

Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound

Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2(I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done byin situ1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceedviaη3-allyl complex formation or ally ether intermediate. The alkylation takes placeviaonly ether intermediate. The resulting allylated and alkylated products have been used for the synthesis of eleven new trisubstituted pyrazoles and one pyrazolone.

Biocatalytic dynamic kinetic reductive resolution with ketoreductase from: Klebsiella pneumoniae: The asymmetric synthesis of functionalized tetrahydropyrans

Ketoreductase from growing cells of Klebsiella pneumoniae (NBRC 3319) acts as an efficient reagent for converting racemic α-benzyl/cinnamyl substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99 %). The reactions described herein followed a biocatalytic dynamic kinetic reductive resolution (DKRR) pathway, which is reported for the first time with such substrates. It was found that the enzyme system can accept substituted mono-aryl rings with different electronic natures. In addition, it also accepts a substituted naphthyl ring and heteroaryl ring in the α-position of the parent β-ketoester. The synthesized enantiopure β-hydroxy esters were then synthetically manipulated to valuable tetrahydropyran building blocks.

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,

MMZNiY-Catalyzed Tsuji–Trost Type of Reaction: A Selective Mono/Bis Allylation of Dicarbonyl Compounds

Abstract: An alternative method to Pd-catalyzed Tsuji–Trost reaction is developed and it provides a simpler route for the selective synthesis of a broad range of mono-/bis-allylated and cinnamylated 1,3-dicarbonyl compounds using MMZNiY catalyst at room temperature. Product selectivity can be controlled by the proper choice of catalyst. The catalyst was also well characterized by SEM, TEM, HRTEM, EDAX and X-ray analysis. Other advantages of catalyst like its ease of preparation, functional tolerance and its reusability are also highlighted.

Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans

A new palladium-catalyzed intramolecular oxidative cycloisomerization of readily available starting materials, 2-cinnamyl-1,3-dicarbonyls, has been demonstrated for the creation of structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway. The reaction shows a broad substrate scope with good to excellent yields. Furthermore, a one-pot procedure has been executed by using readily available cinnamyl alcohols and 1,3-diketones. Cinnamyl verit: Palladium-catalyzed intramolecular oxidative cycloisomerization of readily available 2-cinnamyl-1,3-dicarbonyls affords structurally diverse 2-benzyl furans. The cycloisomerization occurs by a regioselective 5-exo-trig pathway, with a broad substrate scope in good to excellent yields. Furthermore, a one-pot procedure is executed by using readily available cinnamyl alcohols and 1,3-diketones

Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions

The Pd-benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji-Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.

Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols: Selective synthesis of monoallylation products

A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.

Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines

A new strategy to open the 2-allyl-2H-azirines by 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) promotion in metal-free conditions affording 1-azatrienes that in situ electrocyclize to the pyridines in good to excellent yields is reported. The reaction displays a broad substrate scope and good tolerance to a variety of substituents including aryl, alkyl, and heterocyclic groups. In addition, one-pot synthesis of pyridines from oximes via in situ formation of 2H-azirines was achieved.

Enantioselective synthesis of 2-arylbicyclo[1.1.0]butane carboxylates

The rhodium-catalyzed reaction of 2-diazo-5-arylpent-4-enoates can be controlled by the appropriate choice of catalyst and catalyst loading to form either 2-arylbicyclo[1.1.0]butane carboxylates or cyclohexene derivatives. Both products are produced in a

A convergent general strategy for the functionalized 2-Aryl cycloalkylfused chromans: Intramolecular hetero-diels-alder reactions of ortho-quinone methides

(Figure Presented) Five and six: 3, 4-Cyclopentyl- and cyclohexyl-fused 2-arylchromans could be readily prepared from the intramolecular hetero-Diels-Alder reactions of the corresponding ortho-quinone methide (o-QM) precursors tethered to the styrenes under mild reaction conditions. The products were obtained with good to excellent diastereoselectivity (up to > 99:1 dr; see scheme; MOM = methoxymethyl).