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. © 2011 American Chemical Society.
BH3-promoted stereoselective β-lithiation of N-alkyl-2-phenylaziridines / Azzena, U.; Dettori, G.; Pisano, L.; Musio, B.; Luisi, R.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 76:7(2011), pp. 2291-2295. [10.1021/jo102474u]
BH3-promoted stereoselective β-lithiation of N-alkyl-2-phenylaziridines
Musio B.;
2011-01-01
Abstract
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. © 2011 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
