90540-43-5Relevant academic research and scientific papers
A New Method of α-Functionalization for Tertiary Amines by Nucleophilic Substitution of α-Siloxy Amines
Tokitoh, Norihiro,Okazaki, Renji
, p. 735 - 740 (1988)
α-Siloxy amines, which were easily prepared by "silicon Polonovski reaction" of tertiary amine N-oxides with trialkylsilyl trifluoromethanesulfonate, were treated with various nucleophiles to give the corresponding α-functionalized tertiary amines in moderate to good yields.This new method has to the advantage that it enables the α-substitution of amines not only by alkyl groups but also by alkenyl and aryl groups with sp2 carbon as a reaction center, since the introduction of such groups is difficult in electrophilic substitution of dipole-stabilized α-lithio amines.Besides the organometallics such as Grignard and organoaluminum reagents, trimethylsilyl cyanide and silyl enol ether could also be employed as nucleophiles in the presence of an appropriate Lewis acid.
A NEW SYNTHESIS OF α-CYANOAMINES. LEWIS ACID PROMOTED NUCLEOPHILIC SUBSTITUTION OF α-SILOXYAMINES USING TRIMETHYLSILYL CYANIDE
Tokitoh, Norihiro,Okazaki, Renji
, p. 241 - 242 (2007/10/02)
α-Siloxyamines obtained from tertiary amines via their N-oxides were treated with titanium tetrachloride and trimethylsilyl cyanide to give α-cyanated tertiary amines in good yields.
