Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Lewis Acid-Catalyzed Nucleophilic Addition of Indoles to in Situ-Generated 2-Amidoallyl Cations

Lewis Acid-Catalyzed Nucleophilic Addition of Indoles to in Situ-Generated 2-Amidoallyl Cations
Christoph Schneider, Marcel Schlegel
We report herein the first Lewis acid-catalyzed generation of 2-amidoallyl cations through ring-opening of 4-benzylidene-2-oxazolines with Sc(OTf)3. Upon nucleophilic addition of indoles, indolylenamides were obtained with yields of 60–99% and excellent (Z)-selectivity. In addition, the novel strategy was also successfully applied to pyrroles and naphthols as π-nucleophiles. A Brønsted acid-catalyzed process using TfOH formed in situ was ruled out by control experiments.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00791

DOI: 10.1021/acs.joc.7b00791

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