I recently learned about the Stork enamine alkylation method of adding electrophiles to the beta carboxyl position on a molecule. But I can't seem to find out why a direct synthesis is not possible (or perhaps favoured).

I've used an online resource to draw a mechanism that I thought would work, but clearly because we use the Stork enamine method I am missing something here and this can't be true.

Is it perhaps that the double bond is too weak of a nucleophile to attack?

enter image description here

  • $\begingroup$ Your final, hypothetical product should be a keto alcohol, not a diol. Your question needs to be more focused. $\endgroup$ – user55119 Dec 8 '20 at 22:40
  • $\begingroup$ A simple Google search provides: en.wikipedia.org/wiki/Stork_enamine_alkylation $\endgroup$ – Zhe Dec 8 '20 at 22:49
  • $\begingroup$ Aldol condensations like what you've drawn usually need some source of base or acid. The latter would probably be disastrous here, but for example, you could generate the enolate with LDA / NaHMDS etc. before adding the electrophile, and I think sometimes hydroxymethylations with formaldehyde are carried out that way (although you probably can't add formaldehyde itself, see en.wikipedia.org/wiki/Formaldehyde#Forms). I am pretty sure Clayden has a chapter on this. $\endgroup$ – orthocresol Dec 9 '20 at 1:41

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.