4.7 Article

Iodobenzene diacetate/tetrabutylammonium iodide-induced aziridination of N-tosylimines with activated methylene compounds under mild conditions

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 10, Pages 1526-1530

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800157

Keywords

cycloaddition; hypervalent compounds; imines; methylene compounds; nitrogen heterocycles; oxidation

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Aziridination of N-tosylimines with activated methylene compounds induced by iodobenzene diacetate [PhI(OAc)(2)] and tetrabutylammonium bromide [Bu4NBr] afforded the corresponding 2,2-difunctionalized aziridines in good yields with the aid of a catalytic amount of base. The reaction is hypothesized to proceed via a tandem nucleophilic addition-oxidative cyclization pathway.

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