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Synfacts 2009(10): 1156-1156
DOI: 10.1055/s-0029-1217941
DOI: 10.1055/s-0029-1217941
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Intermolecular Addition of Indoles to Cyclic N-Acyliminium Ions
E. A. Peterson, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information
Publication History
Publication Date:
22 September 2009 (online)
Significance
A highly enantioselective intermolecular addition of indoles to cyclic N-acyliminium ions catalyzed by thiourea Schiff base 1 is presented. Electron-rich and electron-deficient indole nucleophiles are suitable substrates for this transformation. For electron-rich indoles TMSCl is used as an additive, whereas for the addition of electron-deficient indoles BCl3 turned out to be a more efficient additive. A catalytic cycle is proposed, where chlorolactam 2 is anticipated as the actual substrate in the alkylation.