Journal of the American Chemical Society · 2013 · 366 citations · 60 references
Natural SciencesChemistryMedicinal ChemistryBiocatalysisCatalysisOrganic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisHeterocycle SynthesisOrganic SynthesisAsymmetric Heterocycle SynthesisAsymmetric SynthesisCatalytic SynthesisEnantioselective SynthesisIndole ChemistryIndole DerivativesIndole Synthesis
Herein we report the synthesis of pyrroloindolines via a catalytic enantioselective formal [3+2] cycloaddition of C(3)-substituted indoles. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbenoid precursors and the rhodium(II)-tetracarboxylate catalyst Rh2(S-PTAD)4. A variety of aryl-substituted pyrroloindolines were prepared in good yields and with high levels of enantioinduction.
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Huw M. L. Davies, Paul R. Bruzinski, Debra H. Lake et al. · Journal of the American Chemical Society · 1996 · 466 citations