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Full Paper
Copper-Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Substrates: Application of Dynamic Kinetic Asymmetric Transformation (DYKAT)
Article first published online: 9 FEB 2010
DOI: 10.1002/adsc.200900790
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Langlois, J.-B. and Alexakis, A. (2010), Copper-Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Substrates: Application of Dynamic Kinetic Asymmetric Transformation (DYKAT). Adv. Synth. Catal., 352: 447–457. doi: 10.1002/adsc.200900790
Publication History
- Issue published online: 17 FEB 2010
- Article first published online: 9 FEB 2010
- Manuscript Received: 12 NOV 2009
Funded by
- Swiss National Research Foundation. Grant Number: 200020-126663
- COST action D40. Grant Number: SER contract No. C07.0097
- BASF
Keywords:
- allylic alkylation;
- allylic compounds;
- asymmetric catalysis;
- copper;
- nucleophilic substitution
Abstract
The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.