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Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization

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Department of Chemistry MS015, Brandeis University, Waltham, Massachusetts 02454-9110
Cite this: Org. Lett. 2006, 8, 25, 5685–5688
Publication Date (Web):November 9, 2006
Copyright © 2006 American Chemical Society

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    A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C−H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

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