Angewandte Chemie International Edition · 2003 · 183 citations · 16 references
Natural SciencesBiochemistryChemistryBiocatalysisCatalysisOrganic ChemistryCarbonyl ChemistryLigand BindingOrganic SynthesisCatalytic SynthesisEnantioselective SynthesisLactam MacrocyclesLactam Synthesis
A planar-chiral Cu/phosphaferrocene–oxazoline catalyst mediates intramolecular Kinugasa reactions to give tricyclic β-lactams with good enantioselectivity. A variant of the process, in which a postulated enolate intermediate is intercepted with an electrophile in a transformation that generates two CC bonds, a CN bond, two new rings, a carbonyl group, and adjacent tertiary and quaternary stereocenters (see scheme), supports the proposed mechanism.
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Stuart B. Rosenblum, Tram Huynh, Adriano Afonso et al. · Journal of Medicinal Chemistry · 1998 · 355 citations