Azzena, Ugo Gavino and Dettori, Giovanna and Pisano, Luisa and Musio, Biagia and Luisi, Renzo (2011) BH3-promoted stereoselective β-lithiation of N-alkyl-2-phenylaziridines. The Journal of Organic Chemistry, Vol. 76 (7), p. 2291-2295. eISSN 1520-6904. Article.
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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.
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