Efficient Synthesis of Chiral Aminocyclopropanes

  • Author: Angewandte Chemie International Edition
  • Published Date: 16 December 2016
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Efficient Synthesis of Chiral Aminocyclopropanes

Enantiopure aminocyclopropanes are important components in biologically active natural products and pharmaceuticals. The most straightforward and atom-efficient route for the construction of chiral aminocyclopropane units is the asymmetric hydroamination of substituted cyclopropenes with amines. However, this transformation is difficult because of the easy ring-opening of the highly strained cyclic skeleton.

Zhaomin Hou and colleagues, RIKEN, Saitama, Japan, have developed an enantioselective hydroamination of substituted cyclopropenes (e.g., 3-methyl-3-phenylcyclopropene) with various amines. They used chiral half-sandwich rare-earth-metal catalysts with yttrium, lanthanum, and samarium (pictured).

This method constitutes a 100 % atom-efficient route for the synthesis of a variety of chiral aminocyclopropane derivatives in high yields (up to 96 %) and excellent stereoselectivity (up to >20:1 d.r. and 99 % ee) under mild reaction conditions (25 °C). According to the researchers, these complexes could be a platform for asymmetric catalysis beyond hydroamination.


Article Views: 2797

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