109685-22-5

Upstream product

• 109685-15-6 3-Hydroxy-4-methoxy-4-(4-methoxy-phenylamino)-2,2-dimethyl-3-phenyl-butyric acid methyl ester 
• 85433-67-6 methyl lithioisobutyrate 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 1074-12-0 phenylglyoxal hydrate 
• 104-94-9 4-methoxy-aniline 
• 78146-52-8 phenylglyoxal monohydrate 
• 91851-03-5 4-methoxy-N-(α-methoxyphenacyl)aniline 
• 131856-80-9 Methyl 3-hydroxy-2,2-dimethyl-4-(p-methoxyphenyl)imino-3-phenylbutanoate 
• 547-63-7 Methyl isobutyrate 

Relevant academic research and scientific papers

Mannich-type reaction catalyzed by HBF4 in water: Effect of the loading of surfactant

The HBF4 (0.1 equiv)-catalyzed Mannich-type reactions of ketene silyl acetals with aldimines proceeded smoothly in water in the coexistence of as low as 1 mol% of SDS. Furthermore, the Mannich-type reaction also took place in water in the absence of SDS by means of 0.3 equiv of HBF4 to afford the corresponding β-amino esters in high yields.

Mannich-type reaction in water in the presence of a surfactant

The effect of sodium dodecyl sulfate (SDS) loading in fluoroboric acid catalyzed Mannich-type reactions of ketene silyl acetals with aldimines was studied. The reaction proceeded smoothly in the presence of 1 mol% of SDS. Formation of small particles was observed by transmission electron microscopy. Georg Thieme Verlag Stuttgart.

Regiocontrolled nucleophilic addition to the carbonyl and imino groups in the reaction of 2-arylamino-2-methoxy-1-phenylethanones with simple lithium ester enolates

The nucleophilic addition of lithium ester enolates 3 to 2-arylamino-2-methoxy-1-phenylethanones I (synthetic equivalents of the related phenylglyoxal anils 2) Is reported. While enolates derived from α,α-dialkyl methyl esters, 3a and 3b, give addition products by attack at either the carbonyl (kinetic products) or the imino groups through a thermally controlled process, those derived from methyl dimethoxyacetate, methyl acetate and methyl propionate, 3c, 3d, and 3e. respectively, only lead to addition products to the carbonyl group. On the basis of the Isolation of all these compounds as stable products and of some transformations and crossover experiments a reasonable mechanism Is proposed for the whole process. In all cases, addition products at the imino groups can also be obtained by the SiO2-catalyzed rearrangement of the corresponding kinetic addition compounds. The synthesis of some substituted 4-benzoyl-β-lactams 8a-g Is a particularly significant feature of this work.

REGIOCONTROLLED ADDITION IN THE REACTION OF N-(α-METHOXYPHENACYL)ANILINES WITH METHYL LITHIOISOBUTYRATE

Reaction of various para-substituted N-(α-methoxyphenacyl)anilines with lithioisobutyrate in excess gives, in good yield, compounds 2-6 through a regiocontrolled process.