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Palladium(0)-Catalyzed Enantioselective C[BOND]H Arylation of Cyclopropanes: Efficient Access to Functionalized Tetrahydroquinolines

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  • This work was supported by the European Research Council under the European Community’s Seventh Framework Program (FP7 2007–2013)/ERC Grant agreement no. 257891. We thank Dr. R. Scopelliti for X-ray crystallographic analysis of compound 3 e.

Abstract

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Activated: The title reaction proceeds efficiently with 1 mol % of palladium and gives tetrahydroquinolines in excellent enantioselectivities (see scheme). The enantiodiscriminating concerted metalation–deprotonation step occurs via a rare seven-membered palladacycle. The cyclopropyl-substituted tetrahydroquinolines can be regioselectively and enantiospecifically reduced to chiral tetrahydrobenzoazepines.

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