Asymmetric Synthesis of α,α,α-Disubstituted N-Alkyl Allyl Amines

  • Author: ChemViews Magazine
  • Published Date: 06 August 2017
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Asymmetric Synthesis of α,α,α-Disubstituted N-Alkyl Allyl Amines

Chiral α,α-disubstituted allylic N-alkyl amines are important building blocks in organic synthesis and medicinal chemistry. However, to date, there is no general synthesis approach.

Arjan W. Kleij, Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Tarragona, Spain, and colleagues have reported the first asymmetric synthesis of α,α,α-disubstituted N-alkyl allyl amine scaffolds. The synthesis uses palladium catalyzed allylic substitution, is user-friendly, and can be done under mild and additive-free conditions.

The scope of the product is the widest reported so far for these allylic amine scaffolds. High asymmetric induction with the enantiomeric ratio (er) up to 98.5:1.5 are found. The use of less reactive anilines is also feasible providing enantioenriched α,α,α-disubstituted N-aryl allylic amines.

According to the researchers, their synthesis method is the most effective method reported to date, although some substrate combinations deliver moderately high asymmetric induction levels and some limitations are pertinent to the allylic precursors. In addition, their work highlights the key role of steric modulation in the allylic substrate to prepare chiral allylic amines via palladium catalysis.

Article Views: 3185

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