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Synfacts 2009(3): 0299-0299  
DOI: 10.1055/s-0028-1087756
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Asymmetric Meerwein-Eschenmoser Rearrangement

Contributor(s): Mark Lautens, Praew Thansandote
E. C. Linton, M. C. Kozlowski*
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

The authors describe the first asymmetric catalytic Meerwein-Eschenmoser Claisen rearrangement. A palladium(II) catalyst was used with a variety of chiral ligands to give chiral allyl oxindoles in good yields and moderate to good enantioselectivities. The phosphino­oxazoline ligand t-BuPHOX (C) seems to be the most general ligand for this transformation.