880-65-9

Basic information

• Product Name: (-)S β-hydroxy β-phenyl n-butanoate de methyle
• Synonyms: (-)S β-hydroxy β-phenyl n-butanoate de methyle
• CAS NO: 880-65-9
• Molecular Weight: 194.23
• Mol File: 880-65-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (-)S β-hydroxy β-phenyl n-butanoate de methyle(CAS DataBase Reference)
• NIST Chemistry Reference: (-)S β-hydroxy β-phenyl n-butanoate de methyle(880-65-9)
• EPA Substance Registry System: (-)S β-hydroxy β-phenyl n-butanoate de methyle(880-65-9)

Safety Data

• Hazardous Substances Data: 880-65-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 141-78-6 ethyl acetate 
• 7210-37-9 (R)-3-hydroxy-3-phenylbutyric acid methyl ester 
• 98-86-2 acetophenone 
• 63741-24-2 α-(p-tolylsulfinyl) β-hydroxy β-phenyl n-butanoate de t-butyle 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 4519-10-2 trichloro<(1-methoxyethenyl)oxy>silane 
• 3759-31-7 3-hydroxy-3-phenylbutanoic acid 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 67-56-1 methanol 
• 1196-67-4 3-phenyl-2-butenal 
• 358-60-1 triethoxyfluorosilane 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 

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 articles and documents

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.].

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.