1051488-22-2

Upstream product

• 487-68-3 mesytaldehyde 
• 3536-96-7 vinylmagnesium chloride 
• 107-02-8 acrolein 
• 2633-66-1 2-mesitylmagnesium bromide 
• 1826-67-1 vinyl magnesium bromide 
• 1052201-89-4 (E)-2-(3-chloroprop-1-enyl)-1,3,5-trimethylbenzene 

Downstream Products

• 2040-15-5 2',4',6'-trimethylpropiophenone 
• 1221972-05-9 acetic acid 1-(2,4,6-trimethyl-phenyl)-allyl ester 
• 1233144-45-0 benzoic acid 1-(2,4,6-trimethyl-phenyl)-allyl ester 
• 1431732-03-4 3-(2,6-dimethoxyphenyl)-1-mesitylpropan-1-one 
• 487-68-3 mesytaldehyde 
• 131534-70-8 E-3-(2,4,6-trimethylphenyl)propenal 
• 107626-95-9 3-phenyl-1-(2,4,6-trimethylphenyl)-1-propanone 
• 102948-50-5 2-benzoyl-1-mesityl-4-phenylbutane-1,4-dione 
• 4456-78-4 1-mesityl-2-propenone 
• 1384176-73-1 methyl 2-diazo-7-mesityl-3,7-dioxoheptanoate 
• 1384176-90-2 methyl 2,3,7-trioxo-7-(2,4,6-trimethylphenyl)heptanoate 
• 1384176-81-1 C₁₇H₂₂O₆ 

Relevant academic research and scientific papers

KOtBu/DMSO Catalytic System for Isomerization of Allylic Alcohols to Ketones

The isomerization of allylic alcohols is an important reaction because it can afford carbonyl compounds in an atom-economical manner. Although base-catalyzed methods are more desirable than those using transition-metal catalysts from both the economic and environmental points of view, these methods have several drawbacks, such as narrow substrate scope and high catalyst loading. This paper reports the development of an efficient KOtBu/DMSO catalytic system suitable for the isomerization of a broad range of allylic alcohols with good yields, to which previously reported systems could not be applied. This catalytic system was successfully applied to a tandem allylic isomerization/electrophilic trapping reaction, thereby highlighting its synthetic utility.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.

Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols

The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.

N-Heterocyclic carbene-catalyzed double acylation of enones with benzils

Thiazolium carbene-catalyzed reaction of aromatic 1,2-diketones with enones in aprotic solvents gave double acylation products in good yields, whereas hydroacylation products formed by Stetter reaction were not detected at all. These results suggested the generation of aroyloxyenamine species from the 1,2-diketones instead of hydroxyenamines (Breslow intermediates). This journal is

Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: Synthesis of highly functionalized cyclopentanones

The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from Χ-keto-α-diazo-β-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Bronsted acid catalysis produces the corresponding 1,2-syn diastereomer.

Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes

Silica gel was found to efficiently promote the rearrangement of allylic acetates into their most stable regioisomers under microwave irradiation. The reaction is easy to perform and eco-friendly. This method was applied to the metal-free synthesis of 1,3-enynes.

FeCl3-catalyzed highly diastereoselective synthesis of substituted piperidines and tetrahydropyrans

The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.

Ruthenium-catalyzed synthesis of allylic alcohols: Boronic acid as a hydroxide source

Secondary allylic alcohols were synthesized from linear allylic halides or carbonates using a catalytic amount of a ruthenium complex in the presence of boronic acid. The effects of solvent, base, ruthenium precursor, and boronic acid were fully explored, and the scope of the reaction was extended to various sub-strates. We also describe a preliminary investigation towards an enantioselective process.

Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds

The catalytic activity of the ruthenium(II) complex [RuCp*(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.