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In all cases tested, the corresponding products were isolated with &gt;95\u2009% <jats:italic>ee<\/jats:italic>s. Methyl alkyl ketones were regiospecifically oxidized at the methylene carbon atom to afford enantiomerically pure \u03b1\u2010aminooxylated ketones. In addition, cyclic ketones could be \u03b1,\u03b1\u2032\u2010dioxidized with remarkably high selectivity, furnishing the corresponding diaminooxylated ketones with &gt;99\u2009% <jats:italic>ee<\/jats:italic>s. The reaction mechanism of the proline\u2010catalyzed direct asymmetric \u03b1\u2010aminooxylation was investigated, and we performed density functional theory (DFT) calculations in order to investigate the nature of the plausible transition states further. We also screened other organocatalysts for the asymmetric \u03b1\u2010oxidation reaction and found that several proline derivatives were also able to catalyze the transformation with excellent enantioselectivities. Moreover, stereoselective routes for the synthesis of monoprotected vicinal diols and hydroxyketones were found. In addition, short routes for the direct preparation of enantiomerically pure epoxides and 1,2\u2010amino alcohols are presented. 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