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Communication
An Asymmetric Organocatalytic Quadruple Cascade Initiated by a Friedel–Crafts-Type Reaction with Electron-Rich Arenes
Article first published online: 28 FEB 2013
DOI: 10.1002/adsc.201201099
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Erdmann, N., Philipps, A. R., Atodiresei, I. and Enders, D. (2013), An Asymmetric Organocatalytic Quadruple Cascade Initiated by a Friedel–Crafts-Type Reaction with Electron-Rich Arenes. Adv. Synth. Catal., 355: 847–852. doi: 10.1002/adsc.201201099
Publication History
- Issue published online: 25 MAR 2013
- Article first published online: 28 FEB 2013
- Manuscript Revised: 30 JAN 2013
- Manuscript Received: 17 DEC 2012
Funded by
- Deutsche Forschungsgemeinschaft. Grant Number: Priority Program Organocatalysis
- Fonds der Chemischen Industrie. Grant Number: Kekulé stipend
- Degussa AG
- BASF
Keywords:
- aniline derivatives;
- asymmetric synthesis;
- domino reactions;
- organocatalysis;
- quadruple cascade
Abstract
An organocatalytic quadruple domino reaction initiated by a Friedel–Crafts-type reaction of electron-rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbaldehydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This diphenylprolinol trimethylsilyl ether-catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo- and excellent enantioselectivity.