Homobimetallic Zinc Hydrophosphonylation Catalysts

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 04 December 2013
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Homobimetallic Zinc Hydrophosphonylation Catalysts

Bifunctional homobimetallic catalysts are attractive for use in organic reactions. C2-symmetry is a generally applied feature of the skeleton in the design of chiral catalysts and chiral zinc compounds are among the most successful catalysts in a variety of asymmetric reactions. Catalytic asymmetric hydrophosphonylation of aldehydes is considerably important in producing biologically active compounds. Neither homobimetallic zinc nor organozinc compounds have been reported for catalyzing asymmetric hydrophosphonylation, although several successful protocols with other catalysts have been disclosed and give high enantioselectivity.

Chao-Shan Da and co-workers, Lanzhou University, China, have reported a C2-symmetric homobimetallic Zn/BINOL-based catalyst (see picture) for the asymmetric hydrophosphonylation of aldehydes. It is interesting that the two identical zinc alkoxides of the catalyst serve two distinct roles. One acts as a Brønsted base and activates the dialkyl phosphonite, and the other acts as a Lewis acid to activate the aldehyde.

This work expands the asymmetric versions of the hydrophosphonylation and offers an interesting insight into future bifunctional catalyst designs.

Article Views: 3369

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH