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Synfacts 2006(3): 0281-0281  
DOI: 10.1055/s-2006-931993
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalyzed Asymmetric Friedel-Crafts Amination of 2-Naphthols

Contributor(s): Benjamin List, Nolwenn J. A. Martin
S. Brandes, M. Bella, A. KjŒrsgaard, K. A. Jørgensen*
Aarhus University, Denmark
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

A highly efficient and enantioselective cinchona-alkaloid organocatalyzed asymmetric Friedel-Crafts amination of 2-naphthols is described. In this reaction different 2-hydroxy-8-amino naphthols 1 react with azodicarboxylate 2 in the presence of a cinchona alkaloid catalyst to form a novel class of non-biaryl atropisomers 4. Using the aminated cinchona alkaloid 3 as catalyst the reaction proceeds with high to excellent yields and excellent enantioselectivities. The formed non-biaryl atrop­isomers 4 can be further elaborated to new chiral molecules.