Acknowledgements are made to the MIUR (Rome), Consorzio C.I.N.M.P.I.S., and University of Bologna. We kindly thank Dr. Paolo Melchiorre (University of Bologna) for helpful discussions.
Enantioselective Phase-Transfer-Catalyzed Intramolecular Aza-Michael Reaction: Effective Route to Pyrazino-Indole Compounds†
Article first published online: 17 MAR 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 17, pages 3238–3241, April 14, 2008
How to Cite
Bandini, M., Eichholzer, A., Tragni, M. and Umani-Ronchi, A. (2008), Enantioselective Phase-Transfer-Catalyzed Intramolecular Aza-Michael Reaction: Effective Route to Pyrazino-Indole Compounds. Angew. Chem. Int. Ed., 47: 3238–3241. doi: 10.1002/anie.200705685
- Issue published online: 8 APR 2008
- Article first published online: 17 MAR 2008
- Manuscript Revised: 25 JAN 2008
- Manuscript Received: 12 DEC 2007
- MIUR (Rome)
- Consorzio C.I.N.M.P.I.S.
- University of Bologna
- asymmetric catalysis;
- Michael addition;
- phase-transfer catalysis
Producing polycycles: A mild and direct stereocontrolled route to pharmacologically active pyrazino-indol-1-ones has been developed. The optimal phase-transfer conditions provide variously functionalized ring-closed compounds in high chemical and optical yields (see scheme; X=H, F, Cl, Me, OMe; Ar=Ph, β-naphthyl; R′=tBu, Et, Me; R=benzyl, para-methoxyphenyl).