European Journal of Organic Chemistry · 2006 · 78 citations · 40 references
Natural SciencesChemistryMedicinal ChemistryGreen ChemistryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisHeterocyclic ReactivityIndole ChemistryIndole DerivativesIndole SynthesisLewis Acid CatalysisLewis AcidityRing-forming Reactions
Abstract A highly diastereoselective Lewis acid (BF 3 · Et 2 O or TiCl 4 ) induced [3+2] cycloaddition of substituted and unsubstituted indoles with 2‐arylcyclopropyl ketones/diesters yielding cyclopenta[ b ]indoles in high yields is reported. This methodology has also been extended to tetrahydrocarbazole, cyclopenta[ b ]‐ and cyclohepta[ b ]indoles affording tetracyclic propellane type frameworks in modest yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
40