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Synfacts 2009(4): 0449-0449  
DOI: 10.1055/s-0028-1088099
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Friedel-Crafts-Type α-Arylation of Aldehydes

Contributor(s): Benjamin List, Ilija Čorić
K. C. Nicolaou*, R. Reingruber, D. Sarlah, S. Bräse
The Scripps Research Institute, La Jolla and University of California, San Diego, USA; , Universität Karlsruhe, Germany
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Publikationsdatum:
23. März 2009 (online)

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Significance

Intramolecular Friedel-Crafts-type α-arylation of aldehydes under SOMO catalysis has been reported. Using the secondary amine catalyst 1 and CAN as the oxidant, aldehydes 2 were obtained in good yields and with high enan­tioselectivity. An application of the method was demonstrated by the total synthesis of the anti­tumor natural product demethyl calamenene.