Linear Allylic Esters Transformed into β-Amino Aldehydes

  • Author: ChemistryViews
  • Published: 21 November 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Linear Allylic Esters Transformed into β-Amino Aldehydes

β-Amino aldehydes can be useful intermediates in organic synthesis, e.g., in the preparation of natural products and or bioactive compounds. They can, for example, be synthesized via an anti-Markovnikov oxidation of allylic amines. However, the necessary substrates can be challenging to obtain. Allylic alcohols might be a useful alternative.


Jian-Ping Qu, Nanjing Tech University, China, Yan-Biao Kang, University of Science and Technology of China, Hefei, and colleagues have developed a tandem isomerization/anti-Markovnikov oxidation that transforms linear allylic imidic esters directly to β-amino aldehydes (pictured). The team used Pd(PhCN)2Cl2 as a catalyst, tert-butyl nitrite as a redox cocatalyst, O2 as the only oxidant, and tert-butanol as the solvent. The reactions were performed at room temperature.

 


The desired β-amino aldehydes were obtained in moderate to good yields. The team found that the use of tert-butanol is important for achieving high aldehyde selectivity. The protocol uses mild conditions and avoids a need for hazardous cocatalysts.


 

 

Article Views: 811

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 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