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

Takaaki Jinzaki, Mitsuru Arakawa, Hidenori Kinoshita, Junji Ichikawa and Katsukiyo Miura*

*Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan, Email:

T. Jinzaki, M. Arakawa, H. Kinoshita, J. Ichikawa, K. Miura, Org. Lett., 2013, 15, 3750-3753.

DOI: 10.1021/ol401663u


α-Alkylated (dimethylsilyl)acetonitriles react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in very good yields. The addition to ketones is effectively promoted by using MgCl2 or CaCl2. (Dimethylsilyl)acetonitrile, which shows lower reactivity, adds efficiently to aldehydes and ketones under catalysis by AcOLi or MgCl2.

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ID: J54-Y2013