This work was financially supported by the ETH research grant TH-01/07-1 and F. Hoffmann-La Roche. We thank Priv.-Doz. Dr. Martin Karpf and Dr. Paul Spurr (both from F. Hoffmann-La Roche, Synthesis and Process Research, Basel) for carefully reading this manuscript and Paul Seiler and Dr. W. Bernd Schweizer (both from ETHZ) for X-ray crystal structure analysis.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
A Highly Strained Planar-Chiral Platinacycle for Catalytic Activation of Internal Olefins in the Friedel–Crafts Alkylation of Indoles†
Article first published online: 15 DEC 2008
DOI: 10.1002/anie.200804944
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Huang, H. and Peters, R. (2009), A Highly Strained Planar-Chiral Platinacycle for Catalytic Activation of Internal Olefins in the Friedel–Crafts Alkylation of Indoles. Angew. Chem. Int. Ed., 48: 604–606. doi: 10.1002/anie.200804944
- †
Publication History
- Issue published online: 29 DEC 2008
- Article first published online: 15 DEC 2008
- Manuscript Received: 9 OCT 2008
Funded by
- ETH. Grant Number: TH-01/07-1
- F. Hoffmann-La Roche
Keywords:
- alkylation;
- hydroarylation;
- metallacycles;
- olefin activation;
- platinum
Activation by deformation: A planar-chiral platinacycle readily prepared by diastereoselective cycloplatination enables the enantioselective intramolecular hydroarylation of indoles having disubstituted Z olefins (see scheme; Ts=p-tolylsulfonyl). Sufficient activity is achieved by a combination of highly strained catalyst geometry and accelerated olefin coordination. This application represents the first highly enantioselective reaction catalyzed by a platinacycle.