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

Ugo Azzena, Giovanna Dettori, Luisa Pisano*, Biagia Musio and Renzo Luisi*

*Dipartimento di Chimica, Universita di Sassari, via Vienna 2, I-07100 Sassari, Italy, Email: luisauniss.it, luisifarmchim.uniba.it

U. Azzena, G. Dettori, L. Pisano, B. Musio, R. Luisi, J. Org. Chem., 2011, 76, 2291-2295.

DOI: 10.1021/jo102474u

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Abstract

BH₃ complexation of N-alkyl-2-phenylaziridines is able to promote a regioselective β-lithiation. The lithiated intermediates were configurationally stable, allowing an enantioselective preparation of cis-2,3-disubstituted aziridines. The structure and stereochemistry of the synthesized BH₃ complexes have been proved with DFT calculations and NMR experiments.

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Key Words

Aziridines

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ID: J42-Y2011-0890