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

页码：1863 / 1868

页数：6

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