Journal
TETRAHEDRON LETTERS
Volume 51, Issue 50, Pages 6594-6597Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.045
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We report on the novel properties of nitrones including their transformations via reactions with sodium malonates to give functionalized stereodefined derivatives of tertiary 3-aminoindoles or anilines, as well as fully-substituted dihydropyrroles. The outcome of the reactions is dependent mainly upon the nature of the starting C-nitrone substituent and solvent used. The formation of a new carbon nitrogen bond in the obtained amines occurs via a nucleophilic 1,2-aryl/3-indolyl shift from C to the adjacent nitrogen. (C) 2010 Elsevier Ltd. All rights reserved.
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