Theoretical and model studies on the chemoselectivity of a Grignard reagentʹs reaction with a combined aminonitrile–oxazolidine system

Semi-empirical quantum chemical studies using PM3 suggest that the preferred reaction between a Grignard reagent and a combined aminonitrile–oxazolidine system involves initial formation of a Lewis acid–base complex between magnesium and the central nitrogen atom, followed by preferred reaction with the aminonitrile function; model studies confirm that this reaction proceeds by addition rather than substitution.