Enantioselective Conjugate Addition – Oppolzer’s sultam auxiliary

Conjugate addition to alpha,beta-unsaturated carbonyls derived from Oppolzer’s sultam


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

The chelation of the carbonyl and sulfonyl oxygen to the magnesium cation restricts the rotation of the acrylamide portion and only S-cis conformation is energetically accessible. Conjugate addition of the organometallic then occurs with high selectivity from underneath to give the R enantiomer only.

W. Oppolzer, Tetrahedron, 1987, 43, 1969–2004.


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