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Synfacts 2007(3): 0322-0322  
DOI: 10.1055/s-2007-968236
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Friedel-Crafts Reaction of Electron-Rich Alkenes

Contributor(s): Benjamin List, Subhas Chandra Pan
M. Terada*, K. Sorimachi
Tohoku University, Sendai, Japan
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Here the authors report a phosphoric acid catalyzed enantioselective Friedel-Crafts reaction of indoles with enecarbamates as imine equivalents. Catalyst 1 (TRIP) has been found to be effective for this reaction when acetonitrile is used as solvent. With 5 mol% of TRIP, moderate to high yields (69-98%) and excellent enantio­selectivities (er = 95:5 to 98:2) are obtained for ­enecarbamates bearing alkyl or aromatic substituents with a variety of indole derivatives.