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.