Stereocontrolled Ring-Opening of Oxazolidinone-Fused Aziridines for the Synthesis of 2‑Amino Ethers

We report a stereocontrolled method for synthesizing 2-amino ethers via the acid-catalyzed ring-opening of oxazolidinone-fused aziridines with alcohols. Mono-, di-, and trisubstituted aziridines all participate in this transformation, with the substitution pattern and the class of alcohol significantly influencing the outcome. High diastereoselectivity was observed with primary and secondary alcohols, while tertiary alcohols often led to elimination or epimerization, depending on the aziridine substrate. This methodology was further applied to the synthesis of the neuraminidase inhibitor A-315675. This method offers a broad scope and high diastereoselectivity in many cases, making it a useful strategy for the construction of 2-amino ether frameworks.