Evans auxilary-controlled enantioselective Diels-Alder reaction

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

The Lewis acid chelates between the carbonyl groups of the dienophile which activates the alkene and locks the conformation so that the bulky isopropyl group blocks one face of the system in the s-cis conformation. Cyclopentadiene undergoes Diels-Alder reaction on the less hindered face.

D. A. Evans, K. T. Chapman and J. Bisaha, J. Am. Chem. Soc., 1988, 110, 1238–1256.

()

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