Trimethylsilyldiazomethane: A Useful Reagent for Generating Alkylidene Carbenes and Its Application to Organic Synthesis
Trimethylsilyldiazomethane: A Useful Reagent for Generating Alkylidene Carbenes and Its Application to Organic Synthesis
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三甲基硅基重氮甲烷：一种有用的亚烷基卡宾生成试剂及其在有机合成中的应用
DOI：
10.1002/chin.199719278
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发表时间：
1996
期刊：
影响因子：
--
通讯作者：
T. Aoyama
中科院分区：
文献类型：
--
作者：
T. Shioiri*;T. Aoyama
三甲基硅基重氮甲烷锂盐（TMSC（Li）N2）与烷基芳基酮和醛通过亚烷基卡宾中间体顺利地反应生成相应的同系炔。在脂族酮的情况下，所得到的亚烷基卡宾可以被胺捕获以提供烯胺，其被有效地转化为同系醛。TMSC（Li）N2还可有效地用于分别由相应的β-酮、α-酮酸的N-甲基苯胺、α-酮酸的N，N-二烷基酰胺和N，N-二取代α-氨基酮制备杂环化合物如2，3-二氢呋喃、环庚[B]吡咯-2-酮和3-吡咯啉。
The lithium salt of trimethylsilyldiazomethane (TMSC (Li) N2) smoothly reacts with alkyl aryl ketones and aldehydes to give the corresponding homologous alkynes via alkylidene carbene intermediates. In the case of aliphatic ketones, the resulting alkylidene carbenes can be trapped by an amine to afford enamines which are efficiently converted to the homologous aldehydes. TMSC (Li) N2 can also be effectively used for the preparation of heterocycles such as 2, 3-dihydrofurans, cyclohepta [b] pyrrol-2-ones, and 3-pyrrolines from the corresponding β-siloxyketones, N-methylanilides of α-keto acids, N, N-dialkylamides of α-keto acids, and N, N-disubstituted α-amino ketones, respectively.