Stork type enamine reactions have proved to be an efficient means for synthesizing alkylated aldehydes.  Challenges in the synthesis include the generation of the requisite enamine, long reaction times and low yields for the alkylations, particularly in the case of low molecular weight aldehydes.  As these alkylation reactions are typically run in polar solvent, we have investigated the use of microwave heating to both reduce the reaction time and improve yield.  Both stepwise synthesis and isolation of the enamine followed by alkylation with a variety of alkylating agents, and tandem enamine synthesis followed by alkylation have been investigated.  The results indicate that with a variety of aldehydes and alkylating agents, shortened reaction times, with yields at least comparable to traditional thermal methods, can be achieved using microwave heating.

Application of microwave methods to the synthesis and alkylation of aldehyde derived enamines

243rd National Meeting (2012)

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