Novel organic catalysts for the direct enantioselective α-oxidation of carbonyl compounds

Abstract

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. © 2005 Elsevier Ltd. All rights reserved.