We thank Kevin Williamson for obtaining X-ray quality crystals of 8, Lara Spencer for determining crystal structures, and Dr. Prakash Raman for insightful discussions. Financial support was provided by the NSF (CHE-0645447) and NIH (GM084022). The NMR spectroscopy facility at UW-Madison is funded by the NIH (S10 RR04981-01) and NSF (CHE-9629688).
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines†
Article first published online: 21 OCT 2010
DOI: 10.1002/anie.201004635
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 49, Issue 48, pages 9153–9157, November 22, 2010
Additional Information
How to Cite
Benkovics, T., Guzei, I. A. and Yoon, T. P. (2010), Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines. Angew. Chem. Int. Ed., 49: 9153–9157. doi: 10.1002/anie.201004635
- †
Publication History
- Issue published online: 17 NOV 2010
- Article first published online: 21 OCT 2010
- Manuscript Received: 27 JUL 2010
Funded by
- NSF. Grant Number: CHE-0645447
- NIH. Grant Number: GM084022
Keywords:
- chiral auxiliaries;
- copper;
- indoles;
- oxaziridines;
- oxyamination
A radical solution: A highly regioselective copper(II)-catalyzed oxyamination of N-acyl indoles with oxaziridines gave aminal products that could be converted in a single step into 3-aminoindoles and 3-aminopyrroloindolines (see scheme). When a chiral N-acyl group was used, the core fragment of some architecturally fascinating pyrroloindoline alkaloids was formed with 91 % ee. Bs=benzenesulfonyl, Moc=methoxycarbonyl.