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Pd-Catalyzed Carboamination of Oxazolidin-2-ones: A Stereoselective Route to trans-2,5-Disubstituted Pyrrolidines

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journal contribution
posted on 21.05.2010, 00:00 by Georgia S. Lemen, John P. Wolfe
Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.