Organic Letters 2005-03-17

Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines.

Shadi Dalili, Andrei K Yudin

Index: Org. Lett. 6th ed., 7 , 1161-1164, (2005)

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Abstract

[reaction: see text] Straightforward methods for palladium-catalyzed alkenylation of aziridines with alkenyl halides and copper-catalyzed alkenylation of aziridines with alkenyl boronic acids have been developed. This methodology offers attractive alternatives to the known methods requiring activated alkenyl halides and acetylenes. A wide variety of N-alkenyl aziridines containing substituents other than electron-withdrawing substituents such as cyano groups and sulfones have been synthesized in good yields. Furthermore, these N-alkenyl aziridines exhibit quite a different reactivity from conventional enamines, as demonstrated by their reactivity.