26735-95-5

Upstream product

• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 20487-40-5 tert-butyl propionate 
• 1663-39-4 tert-Butyl acrylate 
• 100-52-7 benzaldehyde 
• 72658-10-7 tert-butyl trimethylsilyl methyl ketene acetal 

Downstream Products

• 83909-75-5 2-methyl-3-phenyl-1,3-propane diol 
• 104015-38-5 tert-butyl 2-benzoylpropionate 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 83909-76-6 erythro-1-Phenyl-2-methyl-3-tosyloxy-propanol 
• 642098-17-7 tert-butyl 2-fluoro-2-methyl-3-oxo-3-phenylpropanoate 
• 38744-73-9 2,2-dimethyl-3-phenyl-3-oxopropanoic acid 
• 53935-56-1 tert-butyl 2,2-dimethyl-3-oxo-3-phenylpropanoate 
• 118887-71-1 2-azido-2-methyl-1-phenylpropan-1-one 
• 611-70-1 phenyl isopropyl ketone 
• 98831-01-7 (2E)-tert-butyl 2-methyl-3-phenylprop-2-enoate 
• 72658-16-3 tert-butyl 3-hydroxy-2-methyl-3-phenylpropionate 
• 72658-21-0 tert-butyl 3-hydroxy-2-methyl-3-phenylpropionate 

Relevant academic research and scientific papers

Construction of acyclic all-carbon quaternary stereocenter based on asymmetric michael addition of chiral amine

Acyclic asymmetric quaternary stereocenters, which are composed of four carbon-carbon bonds, were finely constructed by utilizing a face-selective alkylation of enolate intermediates derived from an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted (E)-α,β-unsaturated esters. The present face-selective alkylation was able to employ diverse alkyl halides as an electrophile to afford various Michael adducts having an all-carbon quaternary stereocenter. With regard to the deprotection of the chiral auxiliary, N-iodosuccinimide used in our previous study did not work in the present cases; however, we found that pyridine iodine monochloride in the presence of H2O was effective to remove the bornyl group and the benzyl group on the amino group to provide the β-amino ester derivative.

Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds

We report high-performance I+/H2O2 catalysis for the oxidative or decarboxylative oxidative α-azidation of carbonyl compounds by using sodium azide under biphasic neutral phase-transfer conditions. To induce higher reactivity especially for the α-azidation of 1,3-dicarbonyl compounds, we designed a structurally compact isoindoline-derived quaternary ammonium iodide catalyst bearing electron-withdrawing groups. The nonproductive decomposition pathways of I+/H2O2 catalysis could be suppressed by the use of a catalytic amount of a radical-trapping agent. This oxidative coupling tolerates a variety of functional groups and could be readily applied to the late-stage α-azidation of structurally diverse complex molecules. Moreover, we achieved the enantioselective α-azidation of 1,3-dicarbonyl compounds as the first successful example of enantioselective intermolecular oxidative coupling with a chiral hypoiodite catalyst.

A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters by tandem acetylation-E1CB reaction

A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters was developed by improving our previously established method. The new method circumvented the separation of the intermediates, which have an activating group of the hydroxyl group in β-hydroxy esters, furnishing α,β-unsaturated esters in shorter steps than the previous method: an acetylation of β-hydroxy group and subsequent E1cB reaction proceeded in tandem. In addition, the new method can not only employ a diastereomeric mixture of the substrate for the E1cB reaction, it has a wide substrate scope as well, which would enable the synthesis of various trisubstituted (E)-α,β-unsaturated esters.

Surprising role of aryl halides in nickel-catalyzed reductive aldol reactions

A new nickel-catalyzed method for the reductive aldol addition of acrylates and aldehydes has been developed. An unexpected requirement for an aryl iodide additive was found in the process, and the effect was shown to be linked to an initiation step.

Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes As Surfactant Molecules Which Enable Efficient Catalysis in ScCO2

Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO 2, poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO2. In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO2. Formation of emulsions was observed in these reactions, and the systems were studied in detail.

Conjugate addition of lithium enolates to aromatic carbonyl compounds complexed with aluminum tris(2, 6-diphenylphenoxide) (ATPH)

Various lithium enolates of esters undergo effective 1, 6-addition to aromatic carbonyl compounds in the presence of aluminum tris(2, 6-diphenylphenoxide)(ATPH). Thieme.

Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by manganese (II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro and threo-3-hydroxy-2-methyl esters (or amides)

erythro-3-Hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 2-methyl-3-oxo esters or 2-methyl-3-oxo amides in the presence of a catalytic amount of manganese(II) chloride. On the other hand, reduction of these substrates with n-Bu4NBH4 provided threo-isomers selectively. erythro-Selective reduction of 2-methyl-3-oxo amides with NaBH3CN in 1N HCl-MeOH is also described.

Optically Active t-Butyl 2-(p-Tolylsulfinyl)propionate and -butyrate: Synthesis and Relativity in Aldol-type Condensations

The syntheses of optically active t-butyl 2-(p-tolylsulfinyl)propionate and -butyrate (2a and 2b, respectively) are described, and it is shown that aldol-type condensation of the corresponding enolates is limited by steric hindrance.Optically active (2a)