Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions

被引:9
作者
Yoshimura, Fumihiko [1 ]
Abe, Taiki [2 ]
Tanino, Keiji [1 ]
机构
[1] Hokkaido Univ, Dept Chem, Fac Sci, Sapporo, Hokkaido 0600810, Japan
[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan
关键词
nucleophilic addition; nitriles; nitrones; amines; hydroxylamine; TRIMETHYLSILYL; ALKYLATION; ANALOGS;
D O I
10.1055/s-0034-1378274
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of triethylsilyl trifluoromethanesulfonate and triethylamine, aliphatic nitriles undergo addition reactions with aldonitrones under non-basic, mild conditions, providing O-triethylsilyl ethers of beta-N-hydroxyamino nitriles with high yield. The reaction appears to proceed through formation of an N-silyl ketene imine in situ followed by a Mannich-type reaction.
引用
收藏
页码:1863 / 1868
页数:6
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