Methyl alcohol, reaction with oxygen atoms

The use of organomagnesium reagents as bases leads to complexation of the nitrile imines (e.g., 141), which has been found to have a strong effect in promoting syn selectivity in reactions with methyl 2-(l-hydroxyalkyl)acrylates via coordination of the metal atom with the alcoholic oxygen (e.g., leading to the formation of 142). Lithium complexation had little effect (78). 

This is an addition-elimination reaction of methyllithium with iV-methyl-iV-methoxypropionamide forming 2-butanone. As illustrated below using arrow pushing, methyllithium initially adds to the amide. Unlike the process illustrated in Problem 6(f), a second methyllithium does not add and an alcohol is not formed. This is explained by the ability of lithium to coordinate between the two present oxygen atoms. The first is the oxygen of the former carbonyl and the second is the oxygen associated with the methoxy component of the illustrated amide. Due to the stability of this type of five-membered interaction, initial... 

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