Synthesis of alpha-substituted allylic amines via a modified bruylants reaction
Silver tetrafluoroborate, used as an iminium ion promoter from alpha-amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting alpha-amino nitrile was treated with this silver salt prior to its reaction with the vinylic Grignard. This improvement was not observed in the case of acetylenic Grignards. The reactivity of other vinyl organometallics (M = Zn, Li, Al, Cu, Si) was briefly examined.
Agami
C
Laboratoire de Synthese Asymetrique associe au CNRS, Universite Pierre et Marie Curie, 4 place Jussieu, 75005 Paris, France.
Couty
F
Evano
G