Financial support from MIUR, National Projects PRIN 2007 and the University of Perugia and Consorzio CINMPIS, Bari is gratefully acknowledged.
A Highly Enantioselective One-Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence†
Article first published online: 19 AUG 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 40, pages 9382–9385, September 26, 2011
How to Cite
Sternativo, S., Calandriello, A., Costantino, F., Testaferri, L., Tiecco, M. and Marini, F. (2011), A Highly Enantioselective One-Pot Synthesis of Spirolactones by an Organocatalyzed Michael Addition/Cyclization Sequence. Angew. Chem. Int. Ed., 50: 9382–9385. doi: 10.1002/anie.201104819
- Issue published online: 21 SEP 2011
- Article first published online: 19 AUG 2011
- Manuscript Received: 11 JUL 2011
- University of Perugia and Consorzio CINMPIS, Bari
- nucleophilic addition;
- spiro compounds
Spiroring in control: A novel organocatalytic Michael addition/cyclization sequence based on the bis(electrophilic) properties of vinyl selenones has been successfully employed for the synthesis of densely functionalized spirocyclic compounds (see scheme). By using a simple one-pot procedure and mild reaction conditions, spirocyclic compounds were synthesized in high yields and with high levels of enantioselectivity (90–98 % ee).