Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening

A facile synthesis of differently substituted vicinal amino alcohols is reported. We have demonstrated that these amino alcohols could be readily prepared from the oxazolidinones by treatment with aqueous base. We have synthesized a variety of substituted bicyclic aziridine precursors from the corresponding azidoformates using an intramolecular aziridination reaction. The nucleophilic ring opening of these bicyclic aziridines using carbon, oxygen, nitrogen, sulfur, and halogen-containing nucleophiles provided the oxazolidinones in good yield with high regioselectivity. In all cases, nucleophilic attack occurred exclusively at the least substituted carbon of the aziridine ring. Consequently, our approach allows for convenient and rapid access to the vicinal amino alcohol functionality, an important structural component of many natural products.