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Synfacts 2007(4): 0434-0434  
DOI: 10.1055/s-2007-968350
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Indole Alkylations of α,β-Unsaturated Ketones

Contributor(s): Benjamin List, Sebastian Hoffmann
W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen*
Sichuan University, Chengdu and Chengdu Institute of Biology, P. R. of China
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

An organocatalytic enantioselective Michael-type Friedel-Crafts alkylation of indoles 2 with α,β-unsaturated alkyl ketones 1 is reported. The unsaturated ketones 1 are activated as iminium ions, using a chiral primary amine catalyst derived from natural cinchonine. The desired products 3 are obtained in moderate to good enantioselectivities.