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Synfacts 2011(8): 0909-0909  
DOI: 10.1055/s-0030-1260837
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Brønsted Acid Catalyzed N-Functional-ization of Indoles

Contributor(s): Benjamin List, Anna Lee
Y. Xie, Y. Zhao, B. Qian, L. Yang, C. Xia, H. Huang*
Lanzhou Institute of Chemical Physics and Lanzhou University, P. R. of China
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Publikationsdatum:
20. Juli 2011 (online)

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Significance

Huang and co-workers have developed a Brønsted acid catalyzed N-functionalization of indoles with α,β-unsaturated γ-lactams. The authors use α,β-unsaturated γ-lactams as electrophiles since they are easily converted into N-acyliminium ions under the reaction conditions. This concept was applied well to obtain desired chiral N-functionalized indoles in high enantio­selectivities using chiral Brønsted acid catalysts 1a (TRIP) or 1b.