High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines
- 作者：Samuel S. Libendi ; Yosuke Demizu ; Yoshihiro Matsumura ; Osamu Onomura
- 关键词：Cyclic amines ; Methoxylation ; Electrochemical oxidation ; Regioselective
- 刊名：Tetrahedron
- 出版年：2008
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：28 April 2008
- 卷：64
- 期：18
- 页码：3935-3942
- 文件大小：332 K
摘要
N-Protecting groups of 
-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into ′-methoxylated compounds, while N-cyano derivatives changed into -methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the -methoxylated compounds protected with cyano group afforded ,-disubstituted cyclic amines.
-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into ′-methoxylated compounds, while N-cyano derivatives changed into -methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the -methoxylated compounds protected with cyano group afforded ,-disubstituted cyclic amines.