We thank the National Science Foundation and the Institute of General Medical Sciences of the NIH (GM 13 598) for their generous support of our programs and GlaxoSmithKline Research and Development (M.U.F.) for partial postdoctoral fellowship support.
Palladium-Catalyzed Asymmetric Allylation of Prochiral Nucleophiles: Synthesis of 3-Allyl-3-Aryl Oxindoles†
Article first published online: 21 DEC 2004
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 2, pages 308–310, December 27, 2004
How to Cite
Trost, B. M. and Frederiksen, M. U. (2005), Palladium-Catalyzed Asymmetric Allylation of Prochiral Nucleophiles: Synthesis of 3-Allyl-3-Aryl Oxindoles. Angew. Chem. Int. Ed., 44: 308–310. doi: 10.1002/anie.200460335
- Issue published online: 21 DEC 2004
- Article first published online: 21 DEC 2004
- Manuscript Revised: 1 JUN 2004
- Manuscript Received: 15 APR 2004
- asymmetric synthesis;
- homogenous catalysis;
Excellent yields and enantioselectivies are attained in the synthesis of 3-alkyl-3-aryl oxindoles based on the Pd-catalyzed asymmetric allylic alkylation (AAA) reaction. This approach utilizes a nonbasic hydroxylic additive in the transformation of 3-aryl oxindoles into complex, synthetically valuable oxindoles (see scheme).