267884-97-9

Upstream product

• 621-36-3 m-methylphenylacetic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 13910-79-7 2-(3-methylphenyl)acetyl chloride 

Downstream Products

• 266324-84-9 1-(3-methylphenyl)prop-2-en-1-one 
• 1265905-01-8 N-methoxy-N-methyl-2-(3-methylphenyl)propanamide 
• 52629-52-4 1'-(3-methylphenyl)-2'-(4''-chlorophenyl)ethan-2'-one 
• 61263-05-6 dimethyl [3-(3-methylphenyl)-2-oxopropane]phosphonate 
• 494222-28-5 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid 
• 1365392-01-3 C₂₂H₃₁NO₄S 
• 494221-73-7 7-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}heptanoic acid 
• 1365391-71-4 ethyl 7-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}heptanoate 
• 1350720-86-3 4-phenyl-1-(m-tolyl)but-3-yn-2-one 

Relevant academic research and scientific papers

Iron-Catalyzed Michael Addition of Ketones to Polar Olefins

The base metal complex tetrabutylammonium nitrosyltricarbonylferrate {Bu4N[Fe(CO)3(NO)] (TBA[Fe])} – catalyzes the conjugate addition of ketones to polar olefins. The reaction is applicable to a wide range of substrates leading to interesting building blocks for organic synthesis. Clear indications for an acid-base type rather than a C?H activation pathway exist. (Figure presented.).

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis

One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.

Enantioselective Addition of Alkynyl Ketones to Nitroolefins Assisted by Br?nsted Base/H-Bonding Catalysis

Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Br?nsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated.

Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes

Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.

Aerobic Asymmetric Dehydrogenative Cross-Coupling between Two C sp 3 -H Groups Catalyzed by a Chiral-at-Metal Rhodium Complex

A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters. The introduced catalytic asymmetric cross-coupling of two Csp3-H groups with molecular oxygen as the oxidant profits from the oxidative robustness of a chiral-at-metal rhodium(III) catalyst and exploits an autoxidation mechanism or visible-light photosensitized oxidation. In the latter case, the catalyst serves a dual function, namely as a chiral Lewis acid for catalyzing enantioselective enolate chemistry and at the same time as a visible-light-driven photoredox catalyst. Green stuff: A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters by combining asymmetric enolate chemistry with either autoxidation or visible-light photosensitized oxidation. The robustness of a chiral-at-metal rhodium(III) catalyst serves to facilitate the reaction. PMP=para-methoxyphenyl, TFA=trifluoroacetic acid.

Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds

Strong competition: A method for the meta-selective arylation of the highly versatile α-aryl carbonyl motif using diaryliodonium salts is described. In this CuII-catalyzed process the remote carbonyl group is capable of overpowering even strongly para-directing functionalities to form the elusive meta-products (see scheme). Remarkably, the arylation process can also operate under metal-free conditions.

NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS

The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.

Discovery of orally available 8-aza-5-thiaProstaglandin E1 analogs as highly selective EP4 agonists

Analogs 8-aza-16-aryl prostaglandin E1 (PGE1) and 8-aza-5-thia-16-arylPGE1 were synthesized and evaluated with respect to their subtype receptor affinity and EP4 agonist activity for the purposes of identifying sub-type- selective EP

A conformationally reliable spacer for molecular tweezers

A reliable and rigid spacer, trans,trans,trans-perhydronaphthacene, for molecular tweezers was designed. A synthesis and molecular recognition study of its 1,14-disubstituted derivatives was carried out.