Stork reaction

Stork reaction is another reaction just like Mukaiyama reaction that allows to synthesize a thermodynamic product rather than a kinetic product. We've already introduced the topic about competion between thermodynamic and kinetic products in the article about enolates. This time we're not talking about enolate but enamines. If you didn't remind what an enamine is, just think to the name, it is the sum of alkene and amine:


It's the nitrogen analog of an enol.

What we are interested in now is that enamines can act as nucleophiles (just like,again, the silyl enol ether in Mukaiyama reaction) towards an acyl chloride. The result is a positively charged intermediate called iminium ion which can undergo hydrolysis transforming in the corresponding β - dicarbonyl (or 1,3 dicarbonyl) compound:

1,3 dicarbonyl compound are particularly important from a synthetic point of view and that's why we've reported the so called Stork acylation reaction.

First part of the reaction → enamine synthesis

Final part of the reaction → enamine hydrolysis