We thank the NIH for financial support of this work (NIH GM55382 to J.F.H. and GM84584 to L.M.S.) and Johnson-Matthey for gifts of iridium salts.
Iridium-Catalyzed Regio- and Enantioselective N-Allylation of Indoles†
Article first published online: 16 SEP 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 42, pages 7841–7844, October 5, 2009
How to Cite
Stanley, Levi M. and Hartwig, John F. (2009), Iridium-Catalyzed Regio- and Enantioselective N-Allylation of Indoles. Angew. Chem. Int. Ed., 48: 7841–7844. doi: 10.1002/anie.200904338
- Issue published online: 30 SEP 2009
- Article first published online: 16 SEP 2009
- Manuscript Received: 3 AUG 2009
- NIH. Grant Numbers: GM55382, GM84584
- asymmetric catalysis;
- synthetic methods
Iridium is blind to C: Highly regio- and enantioselective, iridium-catalyzed N-allylations of indoles, which complement the more common reactivity of indoles as carbon nucleophiles, have been developed (see scheme). These reactions form highly enantioenriched N-allylindoles, which are readily transformed into enantioenriched 3-(1H-indol-1-yl)-N-methyl-3-aryl propan-1-amines, dihydropyrrolo[1,2-a]indoles, and indol-1-yl propanoic acids.