Abstract
Treatment of N-(N,N-dialkylaminoalkyl)benzotriazoles with 4-bromocrotonates in the presence of zinc provides a new route to 5-(N,N-dialkylamino)-2-alkenoate esters. This is formally the result of the γ-addition of zinc dienolate reagents to iminium cations formed in situ by dissociation of the aminoalkylbenzotriazoles. When N-allyl protecting groups are incorporated into the benzotriazole substrate, deallylation of the tertiary allylamine products gives also a ready access to the corresponding secondary amines.
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