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
来源：
SYNLETT | 2014年 / 25卷 / 13期
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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