The application of silacyclopropane insertion reactivity to the stereoselective synthesis of aminoalcohols is proposed. This project is an extension of the silirane-mediated syntheses of polyoxygenated compounds investigated by the Woerpel group. Regio- and stereoselective insertions of imines and nitrites into theSi-C bonds of siliranes will be developed to form conformationally constrained azasilacyclic compounds with three contiguous stereogenic carbon centers. These products will be elaborated structurally through nucleophilic addition and cyclization reactions that will be controlled stereoelectronically by the conformational preferences of the azasilane ring. Hydroylsis or acylation of the Si-Nbond will then provide the corresponding amine or carbamide, and oxidation of the Si-Cbond will release diastereoenriched 1,3- aminoalcohols. This project is synthetically appealing because it couples simple starting materials to form complicated products using the conformational preferences of a five-membered ring. Aminoalcohols are common motifs in biologically active molecules and this advancement of silirane insertion methodology will provide new approaches for the stereoselective syntheses of nitrogen-containing pharmaceutical targets.
