36057-38-2

Upstream product

• 186581-53-3 diazomethane 
• 1771-65-9 2-methyl-4-oxo-4-phenylbutanoic acid 
• 86044-12-4 2-Methyl-4-oxo-4-phenyl-2-phenylsulfanyl-butyric acid methyl ester 
• 98-88-4 benzoyl chloride 
• 77903-52-7 1-Methyl-c-2-phenyl-t-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 142653-20-1 methyl 2-(tributylstannyl)propionate 
• 100-52-7 benzaldehyde 
• 80-62-6 methacrylic acid methyl ester 
• 36952-37-1 (E)-N-(3-methylpyridin-2-yl)-1-phenylmethanimine 
• 86044-24-8 methyl 2-methyl-4-oxo-4-phenyl-2-butenoate 
• 98-86-2 acetophenone 
• 5445-17-0 Methyl 2-bromopropionate 
• 14990-66-0 1-(1-phenylvinyl)piperidine 

Downstream Products

• 109338-31-0 2-Methyl-4-phenyl-hexen-3-saeure-methylester 
• 108950-48-7 2-Methyl-4-phenyl-hexen-3-saeure 
• 105207-85-0 2-Methyl-4-phenyl-penten-⁽³⁾-saeure 
• 582299-07-8 methyl 3-bromo-2-methyl-4-oxo-4-phenylbutanoate 
• 6366-30-9 methyl 4-oxo-4-phenyl-2,3-cyclopropanobutanoate 
• 343933-14-2 methyl 2-methyl-3-(nitrooxy)-4-oxo-4-phenylbutanoate 
• 1949-38-8 α-Methyl-γ-phenyl-valeriansaeure 
• 132858-55-0 2-methyl-4-phenylhexanoic acid 
• 1771-65-9 2-methyl-4-oxo-4-phenylbutanoic acid 

Relevant academic research and scientific papers

Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide

We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.

Copper-Catalyzed Alkylation of Silyl Enol Ethers with Sterically Hindered α-Bromocarbonyls: Access to the Histamine H3Receptor Antagonist

A general and efficient copper-catalyzed alkylation of silyl enol ethers with functionalized alkyl bromides has been developed for the synthesis of the sterically hindered γ-ketoesters. The transformation was induced through C(sp3)-halogen activation of commercially available sterically hindered alkyl bromides under mild conditions in good results. The strategy could be used for the synthesis of biologically active histamine H3 receptor (H3R) antagonist for medicinal purposes.

Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation

Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild and straightforward conditions.

Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis

A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins.

An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols

We present herein an unprecedented enantioselective isomerization of homoallylic and bishomoallylic secondary alcohols, catalyzed by a commercially available rhodium-complex and a base. This catalytic redox-neutral process provides an effective access to chiral ketones in high efficiency and enantioselectivity, without the use of any stoichiometric reagent or generation of any waste. For the reaction of homoallylic alcohols, this system achieved not only a stereoconvergent access to chiral ketones bearing a β-stereocenter (up to 95%, 86% ee) but also a concomitant oxidative kinetic resolution of the alcohol substrates (S > 20). In the case of bishomoallylic alcohols, an intriguing ligand-induced divergent reactivity was observed. A terminal-to-internal alkene isomerization promoted by Rh/L7 followed by redox isomerization using Rh/BINAP system produced chiral ketones bearing a γ-stereocenter with high yield and enantioselectivity. Mechanistic studies provided strong support for the redox-isomerization pathway with chain walking of the key alkyl-Rh intermediate.

Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation

A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).

A new ferrocenyl bisphosphorus ligand for the asymmetric hydrogenation of α-methylene-γ-keto-carboxylic acids

Upon incorporation of a noncovalent ion pair interaction, a new chiral ferrocenyl bisphosphorus ligand t-Bu-Wudaphos was developed. t-Bu-Wudaphos can be easily synthesized with very high diastereoselectivity as a highly air stable solid. The new ligand exhibited excellent reactivities and enantioselectivities in the asymmetric hydrogenation of α-methylene-γ-keto-carboxylic acids via an ion pair noncovalent interaction (up to >99% conversion, >99% ee).

Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation

Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary-phosphine-oxide) ligand (SPO-Wudaphos) which can enter into both ion pair and H-bond noncovalent interactions. The novel chiral SPO-Wudaphos exhibited excellent results

Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes

A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.