Nucleophilic Addition of 伪-(Dimethylsilyl)nitriles to Aldehydes and Ketones

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• 作者：Takaaki Jinzaki ; Mitsuru Arakawa ; Hidenori Kinoshita ; Junji Ichikawa ; Katsukiyo Miura
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：July 19, 2013
• 年：2013
• 卷：15
• 期：14
• 页码：3750-3753
• 全文大小：217K
• 年卷期：v.15,no.14(July 19, 2013)
• ISSN：1523-7052

文摘

伪-Alkylated (dimethylsilyl)acetonitriles (Me₂HSiCR³R⁴CN) react spontaneously with aldehydes in DMSO to give 尾-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl₂ or CaCl₂. (Dimethylsilyl)acetonitrile (Me₂HSiCH₂CN) shows lower reactivity than the 伪-alkylated analogues. However, the parent reagent adds efficiently to aldehydes and ketones under catalysis by AcOLi or MgCl₂.