Aldol Reaction – Simple Diastereoselectivity Cis gives Syn

Sn2

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

Cis Lithium enolates (Z) generally give Syn Aldol products

In an aldol reaction, cis enolates prefer to form syn aldols. The reaction proceeds via a chair-like transition state where the aldehyde chooses to react with the methyl group equatorial. As the enolate has no choice over its orientation, only a syn product is possible.

C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn and J. Lampe, J. Org. Chem., 1980, 45, 1066–1081.

870

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