Asymmetric intermolecular aldol catalysed by proline – Hydroxyacetone enamine and aldehyde

Sn2

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Asymmetric intermolecular aldol catalysed by S-proline. The reaction goes via a hydroxyacetone enamine, with the -OH group trans to the proline. It attacks the aldehyde on it’s re-facial side to form and anti product. In the chair like transition state the isopropane group is pseudoequatorial to minimise the 1,3-diaxial repulsions from the axial methyl group alpha to the nitrogen. This forms the (S,S)-aldol product, which is anti.

W. Notz and B. List, J. Am. Chem. Soc., 2000, 122, 7386–7387.

J. Liu and L. Wang, Synthesis (Stuttg)., 2016, 49, 960–972.

()

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