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Palladium-Catalysed Cyclisation of Enantiopure Allenic Lactams Prepared from a Pyroglutamic Acid Derived Organozinc Reagent
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1998
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Palladium-catalysed CyclisationUnexpected FormationAsymmetric CatalysisEngineeringOrganic ChemistryInteresting DieneCatalysisChemistryEnantiopure Allene-substituted LactamsSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
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.