66997-66-8

Upstream product

• 22348-96-5 methyl 3-oxodecanoate 
• 76835-64-8 methyl 3-oxododecanoate 
• 67-56-1 methanol 
• 2497-25-8 2-decenal 
• 3913-81-3 (E)-2-decenal 
• 105-45-3 acetoacetic acid methyl ester 
• 186581-53-3 diazomethane 
• 63741-26-4 α-(p-tolylsulfinyl) β-hydroxy n-decanoate de t-butyle 

Downstream Products

• 76905-19-6 methyl (S)-3-(((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl)oxy)decanoate 
• 19526-23-9 3-(S)-hydroxydecanoic acid 
• 1309782-09-9 C₂₃H₃₆N₂O₄ 
• 1309782-18-0 C₃₀H₄₆N₄O₁₀ 
• 1309782-19-1 C₅₈H₇₀N₄O₁₀ 
• 1309781-99-4 C₃₃H₄₉N₅O₁₀ 
• 1309781-97-2 C₃₃H₄₉N₅O₁₀ 
• 1309782-06-6 C₄₇H₆₁N₅O₁₀ 
• 1309781-87-0 C₄₇H₆₁N₅O₁₀ 
• 1309782-17-9 C₃₃H₄₇N₅O₁₀ 
• 1309782-12-4 C₄₇H₅₉N₅O₁₀ 
• 1309781-89-2 C₃₄H₅₀N₆O₉ 
• 1309782-04-4 C₄₈H₆₂N₆O₉ 
• 1309782-03-3 C₄₅H₆₁N₅O₈ 

Relevant academic research and scientific papers

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water

A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

Asymmetric synthesis of secondary alcohols from primary alcohols via intramolecular carbenoid C-H insertion catalyzed by rhodium(II) 3-phenylcholestane-2-carboxylate

Chiral secondary alcohols may be prepared from primary alcohols via asymmetric C-H insertion reactions of α′-alkoxy-α-diazoketones catalyzed by rhodium(II) (2R,3K)-3-phenylcholestane-2-carboxylate.

Over 98% optical yield achieved by a heterogeneous catalysis. Substrate design and analysis of enantio-differentiating factors of tartaric acid-modified Raney nickel hydrogenation

Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94-96% by employing β-keto esters having a proper bulkiness at the γ-position. The γ-bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ-cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.

An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel

The ultrasonic irradiation of Raney nickel catalyst in water followed by the removal of the resulting turbid supernatant gave an excellent nickel catalyst (RNi-U) which generated an asymmetrically-modified nickel catalyst.An EPMA (SEM-EDX) study indicated that RNi-U consisted of a fairly pure nickel surface of homogeneous size.Tartaric acid-NaBr-modified RNi-U (TA-NaBr-MRNi-U) showed a high enantio-differentiating ability as well as reactivity in the hydrogenation of prochiral ketones such as 1,3-diones and 3-oxoalkanoic acid esters.

Highly Efficient Enantio-differentiating Hydrogenation over an Ultrasonicated Raney Nickel Catalyst Modified with Tartaric Acid

A tartaric acid-NaBr-modified nickel catalyst prepared from ultrasonicated Raney nickel showed excellent enantio-differentiating and hydrogenating activity in the hydrogenation of a series of 3-oxoalkanoate and 1,3-diketones.

The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII

The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) over the (R,R)-tartaric acid-NaBr-modified Raney nickel catalyst ((R,R)-TA-NaBr-MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85percent.After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH3(CH2)nCH(OH)CH2COOH, n=0, 6, 8, 10, 12) in a reasonable yield.From the hydrogenation product with (S,S)-TA-NaBr-MRNi, optically pure (S)-3-hydroxyalkanoic acid was obtained by the same process as above.

SYNTHESES ASYMETRIQUES DE β-HYDROXYACIDES PAR CONDENSATION D'ANIONS ENOLATES D'ESTERS α-SULFINYLE CHIRAUX SUR DES COMPOSES CARBONYLES

A stereospecific synthesis of (R)-(+)-t-butyl p-tolylsulfinyl acetate 2 is described.The aldol-type condensation of this reagent leads to β-hydroxyacids in good chemical and optical yields.The determination of the absolute configuration of the condensatio