Chirally Aminated 2‐Naphthols—Organocatalytic Synthesis of Non‐Biaryl Atropisomers by Asymmetric Friedel–Crafts Amination

Sebastian Brandes, Marco Bella, Anne Kjærsgaard, Karl Anker Jørgensen

Angewandte Chemie International Edition · 2006 · 246 citations · 26 references

Concepts

Abstract

Cinchona alkaloids are employed in an organocatalyzed asymmetric Friedel–Crafts amination reaction of 2-naphthols. These amination reactions proceed in high yields with up to 98 % ee and have led to a new class of non-biaryl atropisomer. The rotation barriers of the chiral aminated 2-naphthols have been investigated by experimental and computational methods. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z503042_s.pdf or from the authors. 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

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