Stereoselective Ring-Opening of N-tert-Butanesulfinylaziridines: Access to Acetylenic (alpha)-Amino Alcohols

Ring-opening of enantiopure trans and cis 2,3-disubstituted ethynyl N-tert-butanesulfinylaziridines by water under acidic conditions proved to be highly regio- and diastereoselective, leading to the corresponding enantiopure anti and syn acetylenic (alpha)-amino alcohols. The regio- and stereochemistries were unambiguously determined by NOE experiments through the formation of oxazol­idinone derivatives.