Synthesis of 1,2-Oxazetidines via Cycloaddition

  • Author:
  • Published: 19 October 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Synthesis of 1,2-Oxazetidines via Cycloaddition

Four-membered heterocyclic compounds are useful synthetic intermediates in organic chemistry due to their high reactivity. However, for the same reason, methods for their preparation are sparse and often limited in substrate scope.

Weibing Liu and colleagues, Guangdong University of Petrochemical Technology, Maoming, China, have developed the first regioselective synthesis of polysubstituted 1,2-oxazetidines (pictured). The team used a [2 + 1 + 1] cycloaddition to combine styrenes and arylamines with tert-butyl hydroperoxide (TBHP), which acts both as an oxidant and as the oxygen source for the product. The reaction was performed in dioxane at 70 °C.

The researchers used the developed approach to prepare a broad range of substituted oxazetidines in good yields and with high regioselectivities. The reaction yield is dependent on the electronic nature of substituents on the styrenes: Electron-donating groups lower the yield, while electron-withdrawing substituents have a positive impact.


Article Views: 890

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

Bookmark and Share

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

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH