We gratefully acknowledge the donation of a sample of the ligand (S)-tBu-phox from Prof. G. Helmchen, Heidelberg.
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Communication
Palladium-Catalyzed Synthesis of Substituted Cycloheptane-1,4-diones by an Asymmetric Ring-Expanding Allylation (AREA)†
Article first published online: 19 APR 2007
DOI: 10.1002/anie.200604553
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Schulz, S. and Blechert, S. (2007), Palladium-Catalyzed Synthesis of Substituted Cycloheptane-1,4-diones by an Asymmetric Ring-Expanding Allylation (AREA). Angewandte Chemie International Edition, 46: 3966–3970. doi: 10.1002/anie.200604553
- †
Publication History
- Issue published online: 15 MAY 2007
- Article first published online: 19 APR 2007
- Manuscript Revised: 30 JAN 2007
- Manuscript Received: 7 NOV 2006
Keywords:
- allylation;
- asymmetric catalysis;
- carbocycles;
- palladium;
- ring expansion
Graphical Abstract
The right AREA: Functionalized, seven- and eight-membered carbocycles are available from an asymmetric Pd-catalyzed decarboxylative fragmentation of strained bicyclo[3.2.0]heptane-2-ones (see scheme, dba=trans,trans-dibenzylideneacetone). The products were formed in a sequence of [2+2] cycloaddition, retro-aldol reaction, and asymmetric allylation of ketone enolates.