108471-82-5

Upstream product

• 108471-68-7 ((Z)-2-Dimethylcarbamoyl-1-phenyl-propenyl)-carbamic acid methyl ester 
• 758-96-3 N,N-dimethyl-propanamide 
• 29879-49-0 4-methyl-3-phenyl-2H-isoxazol-5-one 
• 2680-03-7 N,N-Dimethylacrylamide 
• 100-52-7 benzaldehyde 
• 93-58-3 benzoic acid methyl ester 
• 106013-79-0 2-Dimethylamino-5-methyl-4-phenyl-[1,3]oxazin-6-one 
• 20428-71-1 3-hydroxy-3-phenyl-2,N,N-trimethylpropionamide 

Downstream Products

• 20428-71-1 threo-3-hydroxy-3-phenyl-2,N,N-trimethylpropionamide 
• 20428-71-1 (2RS,3RS)-3-hydroxy-N,N,2-trimethyl-3-phenylpropanamide 

Relevant academic research and scientific papers

Manganese-Catalyzed anti-Selective Asymmetric Hydrogenation of α-Substituted β-Ketoamides

A Mn-catalyzed diastereo- and enantioselective hydrogenation of α-substituted β-ketoamides has been realized for the first time under dynamic kinetic resolution conditions. anti-α-Substituted β-hydroxy amides, which are useful building blocks for the synthesis of bioactive molecules and chiral drugs, were prepared in high yields with excellent selectivity (up to >99 percent dr and >99 percent ee) and unprecedentedly high activity (TON up to 10000). The origin of the excellent stereoselectivity was clarified by DFT calculations.

Nickel-Catalyzed Hydroacylation of Styrenes with Simple Aldehydes: Reaction Development and Mechanistic Insights

The first nickel-catalyzed intermolecular hydroacylation reaction of alkenes with simple aldehydes has been developed. This reaction offers a new approach to the selective preparation of branched ketones in high yields (up to 99%) and branched selectivities (up to 99:1). Experimental data provide evidence for reversible formation of acyl-nickel-alkyl intermediate, and DFT calculations show that the aldehyde C-H bond transfer to a coordinated alkene without oxidative addition is involved. The origin of the reactivity and regioselectivity of this reaction was also investigated computationally, which are consistent with experimental observations.

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.

The Vilsmeier-Haack Reaction of Isoxazolin-5-ones. Synthesis and Reactivity of 2-(Dialkylamino)-1,3-oxazin-6-ones

The Vilsmeier-Haack reaction on isoxazolin-5-ones gives 2-(dialkylamino)-1,3-oxazin-6-ones, and a reaction path is proposed depending on substitution pattern of the isoxazolin-5-ones studied.A thermal equilibrium between the oxazinones, imino ketenes, and vinyl isocyanates is hypothesized to explain most of the chemical reactivity of the 2-(dialkylamino)-1,3-oxazin-6-ones.