Issue 3, 2014

Ir-catalyzed intermolecular asymmetric allylic dearomatization reaction of indoles

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

Supplementary files

Article information

Article type
Edge Article
Submitted
31 Oct 2013
Accepted
18 Nov 2013
First published
19 Nov 2013

Chem. Sci., 2014,5, 1059-1063

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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