This work was supported by the DFG (Emmy Noether Programm, SPP 1179 Organokatalyse). We thank Prof. Carsten Bolm for continued support and Chininfabrik Buchler GmbH, Braunschweig, for alkaloid samples.
Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse Architectures†
Article first published online: 30 MAY 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 27, pages 5164–5167, July 2, 2007
How to Cite
Hintermann, L., Schmitz, M. and Englert, U. (2007), Nucleophilic Addition of Organometallic Reagents to Cinchona Alkaloids: Simple Access to Diverse Architectures. Angew. Chem. Int. Ed., 46: 5164–5167. doi: 10.1002/anie.200701341
- Issue published online: 22 JUN 2007
- Article first published online: 30 MAY 2007
- Manuscript Received: 27 MAR 2007
- cinchona alkaloids;
- Grignard reaction;
- neighboring-group effects;
- nucleophilic addition
Aminal pharm: Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.