Stereoselective Axial Alkylation of Cyclohexanone via Enamine

Picture displaying cyclohexanone alkylation

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

The electrophile (n-PrI must attack from an axial position in order to interact with the pi orbital of the C=C bond. If it attacks from the same face as the t-Bu group, it will form a twist boat conformation which is unstable. If it attacks from the opposite face, it can form a chair where the t-Bu remains equatorial (stable) and the n-Pr is axial. The chair-like transition state is the most stable option.

F. Johnson, Chem. Rev., 1968, 68, 375–413.

 

 

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!

Provided by the