Angewandte Chemie International Edition · 2005 · 176 citations · 51 references
Natural SciencesChemistryCatalysisOrganic ChemistryReaction EngineeringCatalyst PreparationCatalyst SynthesisCatalytic MechanismsCatalytic Reaction MechanismsPhase-transfer Catalysts
A general approach to the catalytic asymmetric aza-Henry reaction has been developed. The combination of a commercially available phase-transfer catalyst (PTC) with a base is able to promote the in situ formation of N-carbamoyl imines from α-amido sulfones and activate nitromethane towards the asymmetric addition reaction, thus furnishing N-carbamoyl-protected β-nitroamines in good yields and with up to 98 % ee (see scheme; PG=protecting group).
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