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Org Lett. 2008 Nov 6;10(21):5023-6. doi: 10.1021/ol802123e. Epub 2008 Oct 9.

Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.

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  • 1Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.


This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl- and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.

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