Highly Enantioselective Direct Organocatalytic α‐Chlorination of Ketones

Mauro Marigo, Stephan Bachmann, Nis Halland, Alan Braunton, Karl Anker Jørgensen

Angewandte Chemie International Edition · 2004 · 148 citations · 38 references

Concepts

Abstract

A C2-symmetric diamine serves as the organocatalyst in an asymmetric α-chlorination reaction of simple ketones (e.g., cyclohexanone, diethyl ketone). Optically active α-chloroketones are formed with excellent enantioselectivities using N-chlorosuccinimide (NCS) as the chlorine source (see scheme). These products have broad synthetic utility, in particular for pharmaceutical applications. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z460462_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

References

38