Enantioselective Hydrogenation of Ketones – Ru(II) mechanism

H2 Hydrogenation Catalysed by Ruthenium (II) Complexes

Sn2

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

Ru(II)-amine ligand based complexes developed by Noyori and co-workers are very active and selective catalysts for the hydrogenation or asymmetric hydrogenation of ketones. This achiral ligand example illustrates how the hydrogen is transferred to the carbonyl.

 

Click for an activated asymmetric enantioselective hydrogenation reaction

 

Further Information:

Sn2

The Ruthenium hydride is formed by adding an alkaline base and a hydride source. When the carbonyl is added hydrogen is transferred from the ruthenium hydride ligand to the carbonyl. There is no interaction of the ruthenium with the carbonyl oxygen during the hydrogenation. Two electrons are lost as the two hydrogen are transferred to the carbonyl to form the propan-2-ol in a pericyclic six-membered transition state. The ruthenium hydride can be produced again with addition of H2.

R. Noyori and T. Ohkuma, Angew. Chemie – Int. Ed., 2001, 40, 40–73.

()

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