880-65-9

Upstream product

• 186581-53-3 diazomethane 
• 2623-23-6 L-menthyl acetate 
• 7210-37-9 (R)-3-hydroxy-3-phenylbutyric acid methyl ester 
• 98-86-2 acetophenone 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 358-60-1 triethoxyfluorosilane 
• 67-56-1 methanol 
• 1196-67-4 3-phenyl-2-butenal 
• 4519-10-2 trichloro<(1-methoxyethenyl)oxy>silane 
• 3759-31-7 3-hydroxy-3-phenylbutanoic acid 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 63741-24-2 α-(p-tolylsulfinyl) β-hydroxy β-phenyl n-butanoate de t-butyle 

Downstream Products

• 7210-37-9 (R)-3-hydroxy-3-phenylbutyric acid methyl ester 
• 79-20-9 acetic acid methyl ester 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon–carbon bond forming reaction

The chemical synthesis of organic molecules involves, at its very essence, the creation of carbon–carbon bonds. In this context, the aldol reaction is among the most important synthetic methods, and a wide variety of catalytic and stereoselective versions have been reported. However, aldolizations yielding tertiary aldols, which result from the reaction of an enolate with a ketone, are challenging and only a few catalytic asymmetric Mukaiyama aldol reactions with ketones as electrophiles have been described. These methods typically require relatively high catalyst loadings, deliver substandard enantioselectivity or need special reagents or additives. We now report extremely potent catalysts that readily enable the reaction of silyl ketene acetals with a diverse set of ketones to furnish the corresponding tertiary aldol products in excellent yields and enantioselectivities. Parts per million (ppm) levels of catalyst loadings can be routinely used and provide fast and quantitative product formation in high enantiopurity. In situ spectroscopic studies and acidity measurements suggest a silylium ion based, asymmetric counteranion-directed Lewis acid catalysis mechanism.

Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone

Abstract: Two methods for the synthesis of new axially chiral bipyridine N,N′-dioxides based on catalytic [2+2+2] cyclotrimerization of diynes with nitriles were developed. The N,N′-dioxides were used as catalysts in enantioselective allylation of benzaldehyde with allyltrichlorosilane and aldol reaction of trichlorosilyl ketene acetal of methyl acetate with acetophenone. Graphical abstract: [Figure not available: see fulltext.].

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.

Catalytic enantioselective aldol reaction to ketones

An enantioselective aldol reaction between ketones and ketene silyl acetals is described using CuF-chiral phosphine as a catalyst. The key for high enantioselectivity was the development of a novel ligand derived from Taniaphos combined with the unique ac

New chiral bis(diphenylphospholane) ligands: Design, synthesis, and application to catalytic enantioselective aldol reaction to ketones

New chiral bidentate diphenylphospholanes were designed targeting a catalytic enantioselective aldol reaction to ketones. Ligands 5l and 5m having cis-2-butenyl and cyclopropyl groups at the linker part, respectively, were identified as effective chiral ligands for a CuF-catalyzed enantioselective aldol reaction to ketones. Catalysts prepared from CuF?3PPh 3?2EtOH and these ligands produced ketone aldol products with up to 66% ee, which is promising particularly for this extremely difficult and important catalytic enantioselective carbon-carbon bond forming reaction. The enantioselectivity was strongly dependent on the linker structure. Construction of a deep chiral pocket around the copper metal with stable bidentate chelation is the key to meaningful enantioinduction.

Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones

The catalytic enantioselective addition of an acetate enolate equivalent to ketones is described. Methyl trichlorosilyl ketene acetal reacts with a wide range of ketones in the presence of pyridine N-oxide to afford the aldol addition products in excellen

Catalytic, enantioselective aldol additions to ketones

Catalytic, enantioselective additions of a trichlorosilyl ketene acetal to ketones have been demonstrated. The trichlorosilyl enolate of methyl acetate undergoes a rapid and high-yielding aldol addition to a wide range of ketones (aromatic, olefinic, acet

Stereoselective Aldol Reaction with Chiral Secondary Acetamides

The deprotonated acetamides 4a - c and 5a - c are added to prochiral carbonyl compounds.The influence of the solvent, of the reaction temperature, and of the enolate gegenion on the ratio of the isomeric products 8/9, 18/19, and 26/27, respectively, are studied.The highest degree of diastereoselectivity are observed, when the titanium enolate of the acetamide 4a or the threefold deprotonated N-acetyl-α-phenylglycinol (5a) is used.The diastereomers 18a - d, formed in excess in the addition of 5a to aldehydes, are isolated in pure from by a single recrystallization, and afford the enantiomerically pure β-hydroxy carboxylic acids 3a - d.Thereby, the chiral auxiliary, α-phenylglycinol (14), is recovered.

Asymmetric Synthesis of β-Hydroxy Esters by Reformatsky Reaction and Amide Base Mediated Condensations

Chiral lithium dialkylamides have been used as bases in asymmetric condensation reactions between acetates and ketones.Generally, the asymmetric inductions obtained from these chiral bases were low.Under the experimental conditions used, lithium ester enolates generated from amide bases and acetates of chiral alcohols gave higher optical yields of 1, and in most cases also of 2, than did the Reformatsky reagents obtained from zinc and bromoacetates of the same chiral alcohols.

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