Stereoselective dihydroxylation reactions of γ-amino-α,β-unsaturated estersvia their arylketimine derivatives

Abstract

OsO₄-catalysed dihydroxylation reactions of the aryl ketimine derivatives of (E)-γ-amino-α,β-unsaturated esters gave anti selectivity ranging from 6.7 ∶ 1 to 19 ∶ 1, whereas the opposite syn selectivity was consistently observed with those of (Z)-γ-amino-α,β-unsaturated esters (5.4 ∶ 1 to >100 ∶ 1).