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Tandem Dianionic Dioxy-Cope Rearrangement and Aldol Condensation: A Single-Pot Enantioselective Route to trans-4,5-Disubstituted 1-Cyclopentenecarbaldehyde from Acyclic Bisallylic Compounds
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1992
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Dianionic Dioxy-cope RearrangementEnantioselective SynthesisEngineeringAldol CondensationSingle-pot Enantioselective RouteNatural SciencesDiversity-oriented SynthesisBis-enolate IntermediateComplete Chirality TransmissionOrganic ChemistryStereoselective SynthesisChemistryAsymmetric CatalysisSynthetic ChemistryBiomolecular EngineeringAcyclic Bisallylic Compounds
The first example of dianionic dioxy-Cope rearrangement is presented. A dioxyanion prepared from a C 2 symmetric dienediol [(S,S)-1,8-bis(benzyloxy)-2,6-octadiene-4,5-diol (1)] with sodium bis(trimethylsilyl)amide undergoes a dioxy-Cope rearrangement to generate bis-enolate intermediate I 2, which, on protonation, followed by aldol reaction and base-promoted dehydration, gave (4R,5S)-4,5-bis(benzyloxymethyl)-1-cyclopentenecarbaldehyde [(-)-3] with complete chirality transmission from 1.