Synlett · 1998 · 36 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisMacrocycle SynthesisOrganic SynthesisEnantioselective CatalysisEnantioselective SynthesisLactam SynthesisOrganometallic CatalysisOrganozinc CompoundsOrganozinc CouplingOrganozinc SynthesisPalladium Catalysts
A route for the synthesis of enantiopure allene-substituted lactams has been developed. The key-step involves the copper(I) mediated SN2′ substitution of propargylic tosylates by a (S)-pyroglutamic acid derived organozinc reagent. Pd-catalysed reaction of these allenes with iodobenzene afforded enantiopure bicyclic enamides. Furthermore the unexpected formation of an interesting diene is reported.