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. Author manuscript; available in PMC: 2011 Oct 30.
Published in final edited form as: Tetrahedron. 2010 Oct 30;66(44):8485–8493. doi: 10.1016/j.tet.2010.08.075

Table 3.

Alkylation and Rearrangement of Tertiary Allylic Amines

graphic file with name nihms-235001-t0006.jpg
Compound Amine group
(Z)		 Ar group EWG %Yield of Rearranged
Amine (18)
18a pyrrolidinyl 4-methoxyphenyl CO2Et 83
18b dimethylamino 4-chlorophenyl CO2Et 90
18c dimethylamino 4-methoxyphenyl CO2Et 54
18d dimethylamino 4-bromophenyl CO2Et 70
18e dimethylamino phenyl CO2Et 67
18f dimethylamino 3,4-dimethoxyphenyl-
phenyl		 CO2Et 62
18g dimethylamino naphthyl CO2Et 72
18h piperidinyl 4-methoxyphenyl CO2Et 40
18i dipropylamino 4-methoxyphenyl CO2Et 20
18j dimethylamino 4-methoxyphenyl 4-bromo-
benzoyl		 49
18k dimethylamino 4-methoxyphenyl benzoyl 76
18l dimethylamino 4-methoxyphenyl 4-nitrobenzoyl 82
18m dimethylamino 4-methoxyphenyl 2-nitrophenyl 21
18n dimethylamino 4-methoxyphenyl 4-nitrophenyl 53