Reversible Diels-Alder Reactions for More Enantioselectivity

  • Author: Charlotte Brückner
  • Published Date: 15 October 2012
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Reversible Diels-Alder Reactions for More Enantioselectivity

Related Societies

Five-membered lactones are natural products that are often produced by microorganisms. Depending on the exact structure, they possess diverse biological functions, ranging from multiple flavor properties to neurobiological effects. If the lactones are chiral, only one of the enantiomers might be responsible for the biological function. Therefore, an enantioselective synthesis of lactones is of great interest.

Jeroen Dickschat and colleagues, University of Braunschweig, Germany, found a new synthetic route towards chiral, substituted lactones with a Diels-Alder/retro-Diels-Alder approach. The scientists prepared an enantiomeric Diels-Alder adduct by using a chiral Lewis acid during the Diels-Alder reaction. As a key step, they carried out a diastereoselective aldoladdition on this Diels-Alder adduct. This allowed them to introduce a second stereocenter. Reversing the effects of the first Diels-Alder reaction with a retro-Diels-Alder reaction removed one stereocenter, leaving behind an enantiomer. Therefore, the researchers accomplished to isolate an almost enantiomerically pure lactone from a diastereoselective key reaction.

Article Views: 3852

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, please contact us first for permission and consult our permission guidance prior to making your request

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

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