title: Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones.
abstract: α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR(3)R(4)CN) react spontaneously with aldehydes in DMSO to give β-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 α-alkylated analogues. However, the parent reagent adds efficiently to aldehydes and ketones under catalysis by AcOLi or MgCl2.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Jinzaki
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Arakawa
authors.forename: Hidenori
authors.initials: H
authors.lastname: Kinoshita
authors.forename: Junji
authors.initials: J
authors.lastname: Ichikawa
authors.forename: Katsukiyo
authors.initials: K
authors.lastname: Miura