Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

  • Author: ChemistryViews
  • Published: 12 April 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

Malonic acid half-oxyesters (MAHOs) and malonic acid half-thioesters (MAHTs) can be converted to ester or thioester enolates, respectively, by decarboxylation under mild reaction conditions, avoiding the use of either strong bases or Lewis acids and thus increasing the environmental compatibility of the transformation.

Sylvie Condon, Marc Presset, and colleagues, Université Paris Est Créteil, CNRS, ICMPE, Thiais, France, have developed a new route for the preparation of β2,3-aminoesters involving an organocatalyzed decarboxylative Mannich reaction. The team began by the optimization of the decarboxylative Mannich reaction between tosyl imines and substituted malonic acids half-oxyesters (SMAHOs).

The tertiary amine, 1,4-diazabicyclo[2.2.2]octane (DABCO), was used as catalyst, and tetrahydrofuran (THF) as solvent. The reaction proceeds under simple reaction conditions and tolerates a broad range of substrates, affording general access to β<sup>2,3</sup>-aminoesters, the syn diastereomer being the major one. An alternative multicomponent protocol has also been developed to increase the overall eco-compatibility of the process.

Article Views: 996

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. more

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