Asymmetric Copper-Catalyzed Reactions of Alkenes

  • Author: Angewandte Chemie International Edition
  • Published Date: 12 March 2017
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Asymmetric Copper-Catalyzed Reactions of Alkenes

Radical processes are one of the most efficient approaches for the transformation of olefins. However, the high reactivity of radical species means that the selective control of carbon radical intermediates is extremely challenging. Enantioselective radical reactions, which remained unexplored for a long time, are atrracting research interest.

Zhenyang Lin, Hong Kong University of Science and Technology, China, Guosheng Liu, Chinese Academy of Sciences, Shanghai, and colleagues have discovered that a bisoxazoline/copper(II) cyanide complex can enantioselectively trap benzylic radicals to provide chiral alkylnitriles (example pictured). This is an efficient method to control the stereoselectivity of radical reactions.

The team performed enantioselective copper-catalyzed intermolecular amino- and azidocyanations of alkenes. Various β-amino nitrile derivatives were obtained with good to excellent enantioselectivity. Such chiral β-amino nitriles commonly exist in natural products and bioactive molecules. They could also be transformed to chiral 1,3-diamines, which are an important class of compounds in organic synthesis.


Article Views: 2865

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