92156-76-8

Upstream product

• 69367-52-8 methyl 2-bromo-3-methylbutanoic ester 
• 100-52-7 benzaldehyde 
• 14664-78-9 β-Hydroxy-α-isopropylbenzenpropionsaeure 
• 108-95-2 phenol 
• 556-24-1 methyl 3-methylbutanoate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 29540-55-4 methyl 2-benzoyl-3-methylbutanoate 

Downstream Products

• 98158-54-4 methyl (E)-2-benzylidene-3-methylbutanoate 
• 29540-55-4 methyl 2-benzoyl-3-methylbutanoate 

Relevant academic research and scientific papers

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.

Dehydrative Decarboxylation of 2,3-Disubstituted 3-Hydroxycarboxylic Acids with Dimethylformamide Acetals - Mechanistic Studies and Preparative Applicability

Dimethylformamide dimethylacetal (2a) converts the threo-3-hydroxycarboxylic acids 4 smoothly into the (E)/(Z)-olefins 7/6 only if R2 is an aryl or vinyl substituent.Althougt the reaction exhibits a distinct (E)-selectivity it cannot be considered as a stereo-controlled olefin synthesis.If R2 is alkyl, 2a generates the methyl esters 10 from 4.The erythro-acids 5 react with 2a to give 43 - 95percent of >98percent sterically pure 7.As the key tranformation on the multistep way from 4/5 to 6/7 the fragmentation of the zwitterionic intermediate 11/20 is postulated.