Highly Enantio- and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives.
Article first published online: 30 OCT 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chemistry - A European Journal
Volume 18, Issue 47, pages 14929–14933, November 19, 2012
How to Cite
Noole, A., Sucman, N. S., Kabeshov, M. A., Kanger, T., Macaev, F. Z. and Malkov, A. V. (2012), Highly Enantio- and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives. Chem. Eur. J., 18: 14929–14933. doi: 10.1002/chem.201203099
- Issue published online: 13 NOV 2012
- Article first published online: 30 OCT 2012
- Manuscript Received: 31 AUG 2012
- RSC. Grant Number: JP090309
- COST-ORCA. Grant Number: CM0905
- asymmetric catalysis;
- cascade reactions;
- spiro compounds
Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2-chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio- and diastereoselectivity (see scheme).