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.