167547-59-3

Upstream product

• 54879-64-0 N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 25364-67-4 ethyl 2-benzoyl-3-(4-methoxyphenyl)acrylate 
• 696-62-8 para-iodoanisole 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 

Downstream Products

• 20566-48-7 2-[(4-methoxyphenyl)methyl]acrylic acid ethyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements

An organocatalytic asymmetric process was reported for the sterically precise construction of C-4 alkenyl substituted pyrazolone derivatives bearing multiple stereoelements. A series of interesting products featuring the union of a centrally chiral pyrazolone moiety and an axially chiral styrene unit were obtained in high yield with excellent diastereoselectivity and enantioselectivity (up to 99% ee, >20?:?1 dr). The process has the characteristics of mild reaction conditions, simple operation and broad substrate scope. The result of gram-scale reaction indicates that the reaction has good practicability.

Enantioselective Enzymatic Reduction of Acrylic Acids

An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- A nd aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).

Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst

An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.

Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of α-Substituted β-Ketoesters via Dynamic Kinetic Resolution

An iridium/f-amphol catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent enantioselectivity (up to >99% enantiomeric excess (ee)). A catalytic model is proposed to explain the stereoselectivity.

Method for preparing alpha-alkyl-beta-ketone ester compound

The invention discloses a method for preparing an alpha-alkyl-beta-ketone ester compound shown as a formula (I). The method comprises the following steps: a 1,4-dihydropyridine ester compound shown asa formua (III) is taken as a reducing agent, and under existence of a Lewis acid catalyst, a compound in a formula (II) is subjected to a reduction reaction to obtain the alpha-alkyl-beta-ketone ester compound shown as the formula (I). The method has the advantages of simple operation, mild condition and environmental protection, and is suitable for a plurality of substrates, and the yield can reach as highest as 95%. By using the method of the invention, a plurality of alpha-alkyl-beta-ketone ester compounds can be efficiently prepared, types of medical intermediates are enriched, and the method has an excellent industrial application prospect.

Thiourea catalysed reduction of α-keto substituted acrylate compounds using Hantzsch ester as a reducing agent in water

The first method for the reduction of α-keto substituted acrylate compounds by Hantzsch ester in water under the catalysis of thiourea has been developed. The products were isolated in moderate to high yields (38-95%). These products are important intermediates in the synthesis of a series of natural products and other biologically active molecules.

Heck reaction of Baylis-Hillman adducts with iodobenzenes using a catalytic amount of Pd/C under solvent-free conditions

The reaction of Baylis-Hillman adducts with iodobenzenes using commercially available palladium-on-carbon as a catalyst under solvent-free conditions afforded the corresponding coupling products, α-benzyl-β-keto esters, in high to excellent yields. The reactions are very efficient.

Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds

The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carbon and sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, β-keto esters, β-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of tosylactivated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1,3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.