Asymmetric reduction of carbonyl with CBS reagent

Asymmetric reduction of carbonyl with CBS reagent

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

This reduction works best when the two carbonyl substituents are well-differentiated sterically – ie Ph and Me. When the carbonyl oxygen is complexed to the boron it becomes electrophilic enough to be reduced by the weak hydride source. The hydride itself is delivered via a six-membered cyclic transition state. The enantioselectivity arises from the preference of the larger carbonyl substitutent for the pseudoequatorial position of the ring.

J. Vargas-Caporali and E. Juaristi, Synthesis (Stuttg)., 2016, 48, 3890–3906.



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