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. 2009 Feb 18;131(6):2086-7.
doi: 10.1021/ja809405c.

Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes

K C Nicolaou  1 , Rüdiger Reingruber, David Sarlah, Stefan Bräse
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Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes

K C Nicolaou et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc. 2009 May 13;131(18):6640

Abstract

Enantioselective organo-SOMO catalysis has, in the last two years, been the subject of considerable development and exploration. A number of new and unique transformations have been reported, such as alpha-allylation, alpha-oxyamination, alpha-enolation, and alpha-vinylation of aldehydes. Herein, we report a modification of this activation mode that involves the intramolecular Friedel-Crafts-type alpha-arylation of aldehydes carrying electron-donating groups on their aromatic nucleus and its application to the total synthesis of demethyl calamenene, a potent cytotoxic agent against human adenocarcinoma A 549.

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