69390-18-7

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 78-93-3 butanone 
• 138895-03-1 2-methyl-1-(4-methylphenyl)-2,3-butadien-1-ol 
• 119346-67-7 ethyl (E)-2-methyl-3-(p-tolyl)acrylate 

Downstream Products

• 27793-07-3 (E)-4-Methyl-1,1-bis-methylsulfanyl-5-p-tolyl-penta-1,4-dien-3-one 
• 1101197-88-9 (S)-4-(4-methylphenyl)-3-methyl-2-butanone 
• 1429119-51-6 C₂₀H₁₉NO 
• 1429119-60-7 C₁₃H₁₇NO 
• 1229231-47-3 (R)-(+)-3-methyl-4-(p-tolyl)but-3-en-2-ol 

Relevant academic research and scientific papers

Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols

Asymmetric hydrogenation of prochiral substrates such as ketones and olefins constitutes an important instrument for the construction of stereogenic centers, and a multitude of catalytic systems have been developed for this purpose. However, due to the different nature of the π-system, the hydrogenation of olefins and ketones is normally catalyzed by different metal complexes. Herein, a study on the effect of additives on the Ir-N,P-catalyzed hydrogenation of enones is described. The combination of benzamide and the development of a reactive catalyst unlocked a novel reactivity mode of Crabtree-type complexes toward C=O bond hydrogenation. The role of benzamide is suggested to extend the lifetime of the dihydridic iridium intermediate, which is prone to undergo irreversible trimerization, deactivating the catalyst. This unique reactivity is then coupled with C=C bond hydrogenation for the facile installation of two contiguous stereogenic centers in high yield and stereoselectivity (up to 99% ee, 99/1 d.r.) resulting in a highly stereoselective reduction of enones.

Acid-catalyzed synthesis of α,β-disubstituted conjugated enones by a Meyer-Schuster-type rearrangement in allenols

A novel, direct and simple methodology to gain access to α,β-disubstituted conjugated enones from α-allenols in a sustainable metal catalysis context, considering the inexpensiveness and environmentally friendliness of iron(III) species and protons, has b

CuH-catalyzed enantioselective 1,2-reductions of α,β-unsaturated ketones

The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.

Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.