N,N-Di-tert-butoxycarbonylallylamines are prepared through a palladium-catalyzed reaction of allylic carbonates with di-tert-butyliminodicarbonate under neutral conditions. Allylic carbonates producing monosobstituted pi-allylpalladium complexes tend to give preferentially diprotected allylic amines with the nitrogen bonded to the less substituted carbon atom in good yields. The reaction rate is relatively fast. With allylic carbonates producing disubstituted pi-allylpalladium complexes, the reaction rate is lower as are the yields. The method is particularly suited for chemoselective amination and sequential amination-alkylation reactions.
THE PALLADIUM-CATALYZED AMINATION OF ALLYLIC CARBONATES WITH DI-TERT-BUTYL IMINODICARBONATE UNDER NEUTRAL CONDITIONS
ARCADI, Antonio;MARINELLI, Fabio
1991-01-01
Abstract
N,N-Di-tert-butoxycarbonylallylamines are prepared through a palladium-catalyzed reaction of allylic carbonates with di-tert-butyliminodicarbonate under neutral conditions. Allylic carbonates producing monosobstituted pi-allylpalladium complexes tend to give preferentially diprotected allylic amines with the nitrogen bonded to the less substituted carbon atom in good yields. The reaction rate is relatively fast. With allylic carbonates producing disubstituted pi-allylpalladium complexes, the reaction rate is lower as are the yields. The method is particularly suited for chemoselective amination and sequential amination-alkylation reactions.Pubblicazioni consigliate
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