Chirally Aminated 2-Naphthols-Organocatalytic Synthesis of Non-Biaryl Atropisomers by Asymmetric Friedel-Crafts Amination

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-02, Vol.45 (7), p.1147-1151
Main Authors: Brandes, Sebastian, Bella, Marco, Kjærsgaard, Anne, Jørgensen, Karl Anker
Format: Article
Language:English
Subjects:
amination
asymmetric synthesis
Friedel-Crafts reaction
naphthols
organocatalysis
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503042