A New Chiral, Cationic β-Amino Alcohol Equivalent: A Variable Approach to Enantiomerically Pure Building Blocks for Hydroxyethylene Isosters

Anodic oxidation of (5S)‐ and (5R)‐2 provides (4RS,5S)‐ and (4RS,5R)‐5‐chloromethyl‐4‐methoxyoxazolidin‐2‐one 3, respectively, in good yields. These are chiral cationic amidoalkylation reagents and, through diastereoselective nucleophilic methoxy group exchange, afford variably functionalized enantiomerically pure amino alcohols 4 as well as 1‐substituted 2,3‐epoxypropylamines 1, which are precursors for peptidomimetics.