36550-86-4

Upstream product

• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 823-76-7 Cyclohexyl methyl ketone 
• 186581-53-3 diazomethane 
• 63741-27-5 α-(p-tolylsulfinyl) β-hydroxy β-cyclohexyl n-butanoate de t-butyle 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 

Relevant academic research and scientific papers

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.

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.

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