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BH3-Promoted Stereoselective β-Lithiation of N-Alkyl-2-phenylaziridines

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journal contribution
posted on 01.04.2011, 00:00 by Ugo Azzena, Giovanna Dettori, Luisa Pisano, Biagia Musio, Renzo Luisi
BH3 complexes of N-alkyl-2-phenylaziridines have been synthesized and their structure and stereochemistry proved with DFT calculations and NMR experiments. It has been demonstrated that the Lewis acid complexation is able to promote a regioselective β-lithiation in 2-phenylaziridino−borane complexes. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstituted aziridines.