We thank Caroline Gawlik for technical support. Furthermore, help from our analytical departments, especially the NMR, HPLC, and MS facilities is gratefully acknowledged. We thank Sanofi-Aventis, the Max-Planck-Society, the DFG (Priority Program Organocatalysis SPP1179), and the Fonds der Chemischen Industrie for funding.
Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions†
Article first published online: 17 DEC 2010
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 3, pages 754–758, January 17, 2011
How to Cite
Ratjen, L., García-García, P., Lay, F., Beck, M. E. and List, B. (2011), Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions. Angew. Chem. Int. Ed., 50: 754–758. doi: 10.1002/anie.201005954
- Issue published online: 12 JAN 2011
- Article first published online: 17 DEC 2010
- Manuscript Revised: 18 OCT 2010
- Manuscript Received: 22 SEP 2010
- Fonds der Chemischen Industrie
- aldol reactions;
- synthetic methods;
Let's talk about six! A new chiral disulfonimide catalyzed vinylogous Mukaiyama aldol addition of crotonic acid derived nucleophiles to aldehydes has been developed and the concept of vinylogy was further expanded to double vinylogous, sorbic acid derived nucleophiles. This reaction is an example of a previously unknown ε-selective bisvinylogous Mukaiyama Aldol addition that extends the substrate by six carbon atoms (see scheme).