A detailed investigation of the opening of epoxides with trimethylsilyl cyanide (TMSCN) and zinc iodide is proposed. The conversion of the products of this stereo-specific and regiospecific reaction to Beta-amino alcohols and oxazolines will be studied. The ring opening of epoxides to Beta-hydroxy isonitrile derivatives with TMSCN - ZnI2 will be extended to other strained heterocyclic rings including aziridines, thiiranes, azetadines, oxetanes and Beta-lactones. The influence of substituents on the regiochemistry of the ring opening process will be evaluated in detail. Attempts will be made to utilize the reactions developed as part of the work to prepare amino sugars. An approach to daunosamine is outlined.
