Conjugate addition of enolates – Overview


An enolate or enol equivalent can be added to an α,β-unsaturated carbonyl compound. This is an example of a simple base-catalysed enolization step:

Click the image to view the 3D animation

Enolate nucleophiles can undergo conjugate addition, but they have exactly the same opportunity to attack the carbonyl group directly as do simple nucleophiles. The same factors also govern the eventual outcome of the reaction. Thermodynamic control leads to conjugate addition, but kinetic control leads to direct attack. The key to successful conjugate addition is to ensure that direct addition to the carbonyl (which is an aldol reaction) is reversible. This enables the conjugate addition to compete and, as its product is more stable, it eventually becomes the sole product.

Click the two different types of reaction to view the 3D animations

A. G. Csákÿ, G. de la Herrán and M. C. Murcia, Chem. Soc. Rev., 2010, 39, 4080.

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the