53439-96-6

Upstream product

• 31197-66-7 isopropyl benzoylformate 
• 924-53-8 isopropyl glyoxalate 
• 98-80-6 phenylboronic acid 
• 122-00-9 para-methylacetophenone 
• 585-74-0 3-Methylacetophenone 
• 577-16-2 2-Methylacetophenone 
• 16208-21-2 2-naphthylglyoxal hydrate 
• 16208-20-1 2-(naphthalen-1-yl)-2-oxoacetaldehyde hydrate 
• 101906-05-2 2,2-dihydroxy-1-[4-(trifluoromethyl)phenyl]ethanone 
• 80352-42-7 1-(4-bromophenyl)-2,2-dihydroxyethanone 
• 4996-21-8 1-(4-chloro-phenyl)-2,2-dihydroxy-ethanone 
• 118888-64-5 1-(2-Chloro-phenyl)-2,2-dihydroxy-ethanone 
• 447-43-8 1-(4-fluorophenyl)-2,2-dihydroxyethan-1-one 
• 362609-92-5 3,4-(methylenedioxy)phenylglyoxal monohydrate 

Downstream Products

• 1190370-09-2 C₁₃H₁₅ClO₄ 
• 1224387-02-3 (2-isopropoxy-2-oxo-(S)-1-phenylethyl) α-bromopropanoate 
• 1224387-08-9 (2-isopropoxy-2-oxo-(S)-1-phenylethyl) α-bromophenylacetate 

Relevant academic research and scientific papers

Preparation method for key intermediate of Barnidipine

he preparation method of the intermediate is characterized by comprising the following steps: with chiral hydroxy acid as a starting material, the chiral hydroxy acid reacts with isopropanol under the catalysis of lewis acid, then reacts with an acetoacetic acid reagent, and is directly cyclized with m-nitrobenzaldehyde and methyl 3-aminocrotonate in an alcohol solvent, then crystallization is performed in a low temperature environment for realizing chiral resolution, hydrolysis is performed by sodium hydroxide, and then acidization is performed by hydrochloric acid to obtain a product. the intermediate is characterized by being prepared by the following steps: with chiral hydroxy acid as a starting material,the chiral hydroxy acid reacts with isopropanol under the catalysis of lewis acid, then reacts with an acetoacetic acid reagent, and is directly cyclized with m-nitrobenzaldehyde and methyl 3-aminocrotonate in an alcohol solvent, crystallization and chiral resolution are realized in a low temperature environment, hydrolysis is performed by sodium hydroxide, and then acidization is performed by hydrochloric acid to obtain a product. The preparation method disclosed by the invention has the advantages that the preparation technology is simple, the resolution is easy, the product yield is high, the optical purity is good, the quality is stable, and the large-scale industrial production is easy.

Chiral-at-Iron Catalyst: Expanding the Chemical Space for Asymmetric Earth-Abundant Metal Catalysis

A new class of chiral iron catalysts is introduced that contains exclusively achiral ligands with the overall chirality being the result of a stereogenic iron center. Specifically, iron(II) is cis-coordinated to two N-(2-pyridyl)-substituted N-heterocycli

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83percent ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex

An asymmetric Meerwein-Ponndorf-Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N′-dioxide/Y(OTf)3 complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.

Dual pathway for the asymmetric transfer hydrogenation of α-ketoimides to chiral α-hydroxy imides or chiral α-hydroxy esters

In an enantioselective reaction, we expect to obtain two types of chiral products through a controllable strategy in asymmetric catalysis. Herein, we develop Ru-catalysed asymmetric transfer hydrogenation of α-ketoimides to realise an enantioselective construction of chiral α-hydroxy imides or chiral α-hydroxy esters. The transformation of α-ketoimides catalysed by (S,S)-[RuCl(η6-mesitylene)diamine] can afford various chiral α-hydroxy imides with high yields and enantioselectivities, whereas that catalysed by (S,S)-[RuCl(η6-hexamethylbenzene)diamine] gives the desirable chiral α-hydroxy esters through a slight adjustment of the reaction conditions. The method described here is a controllable organic transformation with sodium formate as a hydrogen source under mild reaction conditions, and the benefit of this transformation is that various chiral α-hydroxy imides or α-hydroxy esters can be obtained selectively from α-ketoimides. Selective directive: An enantioselective transformation in the Ru-catalyzed asymmetric transfer hydrogenation of α-ketoimides to chiral α-hydroxy imides or α-hydroxy esters is developed. The transformation of α-ketoimides catalyzed by (S,S)-[RuCl(η6-mesitylene)diamine] can afford various chiral α-hydroxy imides with high yields and enantioselectivities, whereas that catalyzed by (S,S)-[RuCl(η6-hexamethylbenzene)diamine] give desirable chiral α-hydroxy esters through a slight adjustment of reaction conditions.

Chiral N,N′-dioxide-FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction

An environmentally benign catalyst, the N,N′-dioxide-FeCl3 complex, has been developed for the asymmetric intramolecular Cannizzaro reaction. Aryl and alkyl glyoxal monohydrates were applied to obtain α-hydroxy acid esters with excellent results. Deuterium-label and control experiments shed light on the reaction mechanism.

Enantio- and chemoselective Br?nsted-acid/Mg(nBu) 2 catalysed reduction of α-keto esters with catecholborane

The first enantio- and chemoselective Br?nsted-acid catalysed reduction of α-keto esters with catecholborane has been developed. The α-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity. This journal is the Partner Organisations 2014.

A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis

An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.

A homochiral porous metal-organic framework for enantioselective adsorption of mandelates and photocyclizaton of tropolone ethers

A chiral porous metal-organic framework of an axially C2- symmetric 1,1′-biphenol ligand is constructed and can be used as a solid-state host to enanioselectively adsorb mandelates with up to 93.1% ee and to entrap achiral tropolone ethers and

Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex

The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl2(PPh3)3 with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities. The Royal Society of Chemistry 2012.