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Tandem Nazarov Cyclization−Michael Addition Sequence Catalyzed by an Ir(III) Complex
88
Citations
9
References
2006
Year
First ExamplesEngineeringHeterocyclicMechanistic FactorsCoordination ComplexOrganic ChemistryOrganometallic CatalysisCatalysisStereoselective SynthesisChemistryHeterocycle ChemistryAsymmetric CatalysisContiguous StereocentersBiomolecular Engineering
The first examples of a tandem Nazarov cyclization/Michael addition process are described. The sequence is efficiently catalyzed by Ir[Me(CO)(dppe)(DIB)]2+ and occurs with high diastereoselectivity, creating three contiguous stereocenters. The mechanistic factors controlling the reactivity and diastereoselectivity are discussed.
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