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Silylcupration and copper-catalyzed carbomagnesiation of ynamides: Application to aza-Claisen rearrangement
Yasui, Hiroto,Yorimitsu, Hideki,Oshima, Koichiro
body text, p. 373 - 379 (2009/04/07)
Treatment of ynamides with silylcopper reagents resulted in silylcupration to afford (E)-ss-silylenamides, after protonolysis, in good yields with high regio- and stereoselectivity. Reaction of ynamides having an allyl group on the nitrogen with Grignard reagents in the presence of a copper catalyst resulted in carbomagnesiation across the alkynyl unit and subsequent heating provided 4-pentenenitriles via aza-Claisen rearrangement.
