Evans auxilary-controlled enantioselective syn Aldol reaction


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

The Z-boron enolate adopts the non-chelated conformation with the imide carbonyl opposite the enolate oxygen. The auxiliary hinders the top face of the enolate so the aldehyde attacks from below to form a chair like transition state. Boron enolate Z-geometry produces the syn product whereas the auxiliary controls facial selectivity and therefore a single enantiomer is formed.

D. a Evans, J. V Nelson and T. R. Taber, J. Am. Chem. Soc., 1981, 103, 3099–3111.


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