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The scope and limitations of the process were established by varying the nature of the alkene and radical precursor. Carbocyanation of chiral allylsilanes was shown to occur with high diastereocontrol, leading to <jats:italic>syn<\/jats:italic> \u03b2\u2010silyl nitriles. The origin of the stereocontrol was rationalized by a Felkin\u2013Anh\u2010type transition\u2010state model. 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