82584-39-2

Upstream product

• 33398-52-6 erythro-3-Hydroxy-4,4-dimethyl-2-phenylvaleriansaeure 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 811-98-3 d⁽⁴⁾-methanol 

Relevant academic research and scientific papers

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.