Abstract
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The proline-derived
N-sulfonylcarboxamide-catalyzed direct enantioselective α-oxidation of ketones and aldehydes with nitrosobenzene is presented. The reactions proceed smoothly furnishing the corresponding α-aminoxylated compounds in good yields with up to >99% ee. The proline-derived
N-sulfonylcarboxamides were also found to be excellent catalysts for the direct enantioselective nitroso Diels–Alder-type reaction between nitrosobenzene and α,β-unsaturated cyclic ketones yielding the corresponding bicyclic Diels–Alder adduct products with up to >99% ee. The proline-derived
N-sulfonylcarboxamides represent a readily available and highly modular novel type of organic catalyst.