A new method of .ALPHA.-functionalization for tertiary amines by nucleophilic substitution of .ALPHA.-siloxy amines.

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概要

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• α-Siloxy amines, which were easily prepared by "silicon Polonovski reaction" of tertiary amine <I>N</I>-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 the advantage that it enables the α-substitution of amines not only by alkyl groups but also by alkenyl and aryl groups with sp<SUP>2</SUP> 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.

• 公益社団法人 日本化学会の論文

著者

• Okazaki Renji

  Department Of Chemical And Biological Sciences Faculty Of Science Japan Women's University

• Tokitoh Norihiro

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

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