The Journal of Organic Chemistry · 2012 · 109 citations · 34 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryMacrocycle SynthesisOrganic SynthesisAsymmetric Heterocycle SynthesisChiral Product SynthesisConfiguration At Chiral CentersEnantioselective CatalysisEnantioselective Synthesis
A Me-DuPhos-catalyzed efficient asymmetric [3 + 2] cycloaddition reaction between Morita-Baylis-Hillman carbonates of isatins and N-phenylmaleimide has been developed. This reaction constructs three chiral centers in one step to afford spirocyclopentaneoxindoles in good yields (up to 84%) with excellent diastereo- and enantioselectivies (up to 99% ee).
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