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Kinetic control of stereochemistry in the addition of unsymmetrical ketens to cyclopentadiene
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1970
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Electrocyclic AdditionEngineeringHeterocyclicBiochemistryNatural SciencesOrganic ChemistryInitial Crosswise ApproachStereoselective SynthesisChemistryHeterocycle ChemistryUnsymmetrical KetensAsymmetric CatalysisKinetic ControlEnantioselective SynthesisBiomolecular Engineering
Assumption of an initial crosswise approach of cyclopentadiene and a keten, combined with simple frontier orbital considerations, leads to a prediction of stereochemistry in the electrocyclic addition which has been confirmed by experiment.