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Issue 3, 2014
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Ir-catalyzed intermolecular asymmetric allylic dearomatization reaction of indoles

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Abstract

An Ir-catalyzed intermolecular asymmetric dearomatization reaction of substituted indoles with allylic alcohols has been realized to afford the corresponding indoline derivatives in 71–97% yield with up to 98% ee in the presence of the Lewis acid Fe(OTf)2. This methodology features the enantioselective construction of all-carbon quaternary stereogenic centers of prochiral nucleophiles and its utility has been demonstrated in the asymmetric total synthesis of (−)-debromoflustramine B.

Graphical abstract: Ir-catalyzed intermolecular asymmetric allylic dearomatization reaction of indoles

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Publication details

The article was received on 31 Oct 2013, accepted on 18 Nov 2013 and first published on 19 Nov 2013


Article type: Edge Article
DOI: 10.1039/C3SC53019A
Chem. Sci., 2014,5, 1059-1063

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    Ir-catalyzed intermolecular asymmetric allylic dearomatization reaction of indoles

    X. Zhang, L. Han and S. You, Chem. Sci., 2014, 5, 1059
    DOI: 10.1039/C3SC53019A

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