Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines.
[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.
Dalili
Shadi
S
Davenport Research Labs, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6 Canada.
Yudin
Andrei K
AK